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Chemical Structure| 483324-01-2 Chemical Structure| 483324-01-2

Structure of 483324-01-2

Chemical Structure| 483324-01-2

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CAS No.: 483324-01-2

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Product Details of [ 483324-01-2 ]

CAS No. :483324-01-2
Formula : C9H6ClN3
M.W : 191.62
SMILES Code : ClC1=NC=CC(C2=CC=CN=C2)=N1
MDL No. :MFCD09743494
InChI Key :MGQROXOMFRGAOY-UHFFFAOYSA-N
Pubchem ID :11805543

Safety of [ 483324-01-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 483324-01-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 50.27
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

38.67 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.85
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.76
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.19
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.71
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.61
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.82

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.75
Solubility 0.338 mg/ml ; 0.00176 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.19
Solubility 1.24 mg/ml ; 0.00646 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.42
Solubility 0.00735 mg/ml ; 0.0000384 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.22 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 2.09

Application In Synthesis of [ 483324-01-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 483324-01-2 ]

[ 483324-01-2 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 626-55-1 ]
  • [ 3934-20-1 ]
  • [ 483324-01-2 ]
  • 2
  • [ 626-55-1 ]
  • [ 1722-12-9 ]
  • [ 483324-01-2 ]
YieldReaction ConditionsOperation in experiment
53% Preparation of 2-chloro-4-pyridin-3-yl-pyrimidine lll-a To a solution of n-butyllithium (2.5 molar in hexane, 13.5 mL, 34 mmol) in anhydrous diethylether (50 mL) under argon at -78 ' was added 3-bromo pyridine (3 mL, 31 mmol). The mixture was stirred for 1 h, then a suspension of 2-chloro pyrimidine (3.6 g, 31 mmol) in anhydrous diethylether (30 mL) was added portionwise over 10 min. The resulting mixture was stirred at -30 C for 30 min, and then allowed to warm to 0 C for 1 h, at which point the reaction was successively quenched by addition of water (1 mL) in THF (10 mL) and DDQ (7.6 g, 34 mmol) in THF (25 mL). The resulting brown suspension was stirred at room temperature for 15 min, then cooled to 0 ', and treated with hexane (25 mL) and aqueous NaOH (3N, 25 mL). The mixture was stirred at 0 ' for 5 min, diluted with water (100 mL) and then extracted with ethyl acetate. The combined organic layers were washed with water, dried on MgS04, and concentrated to a minimum volume to afford after filtration lll-a as a pale brown solid (3.14 g, 53 %). H NMR (400 MHz, DMSO- de) delta 9.35 (dd, J = 2.3, 0.8 Hz, 1 H), 8.90 (d, J = 5.3 Hz, 1 H), 8.79 (dd, J = 4.8, 1 .6 Hz, 1 H), 8.54 (ddd, J = 8.0, 2.3, 1 .7 Hz, 1 H), 8.26 (d, J = 5.3 Hz, 1 H), 7.62 (ddd, J = 8.0, 4.8, 0.8 Hz, 1 H).
  • 3
  • [ 2524-67-6 ]
  • [ 483324-01-2 ]
  • N-(4-morpholin-4-ylphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine [ No CAS ]
  • 4
  • [ 302-84-1 ]
  • [ 483324-01-2 ]
  • 3-hydroxy-2-(4-pyridin-3-yl-pyrimidin-2-ylamino)-propionic acid [ No CAS ]
  • 5
  • [ 98-16-8 ]
  • [ 483324-01-2 ]
  • 4-(3-Pyridinyl)-N-[3-(trifluoromethyl)phenyl]-2-pyrimidinamine [ No CAS ]
  • 6
  • [ 106-47-8 ]
  • [ 483324-01-2 ]
  • N-(4-chlorophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine [ No CAS ]
  • 7
  • [ 104-94-9 ]
  • [ 483324-01-2 ]
  • [ 112675-67-9 ]
  • 8
  • [ 100-01-6 ]
  • [ 483324-01-2 ]
  • N-(4-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine [ No CAS ]
  • 9
  • [ 62-53-3 ]
  • [ 483324-01-2 ]
  • N-phenyl-4-(pyridin-3-yl)pyrimidin-2-amine [ No CAS ]
  • 10
  • [ 328-39-2 ]
  • [ 483324-01-2 ]
  • 4-methyl-2-(4-pyridin-3-yl-pyrimidin-2-ylamino)-pentanoic acid [ No CAS ]
  • 11
  • [ 95-53-4 ]
  • [ 483324-01-2 ]
  • N-(2-methylphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine [ No CAS ]
  • 12
  • [ 122-80-5 ]
  • [ 483324-01-2 ]
  • N-[4-(4-Pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-acetamide [ No CAS ]
  • 13
  • [ 1003316-49-1 ]
  • [ 483324-01-2 ]
  • 6-chloro-N7-(4-(pyridin-3-yl)pyrimidin-2-yl)-N3-(3-(trifluoromethyl)phenyl)benzo[d]isoxazole-3,7-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate;palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 130℃; for 96h; An oven-dried microwave tube was charged with Xantphos (26 mg, 46 mumol) and dioxane (1 ml_). The tube was evacuated under vacuum and then purged with argon, then Palladium(ll) acetate (5.1 mg, 23 mumol) was added, and the mixture was stirred under argon for 15 min. In a separate tube, 2-chloro-4-(pyridin-3- yl)pyrimidine (44 mg, 229 mumol), 6-chloro-N3-(3-(trifluoromethyl)phenyl)benzo[d]isoxazole-3,7-diamine (75 mg, 229 mumol), cesium carbonate (75 mg, 229 mumol), and dioxane (1 ml_) were added. Then Pd (OAc)2/Xantphos solution was added with a syringe and rinsed with dioxane (0.5 ml_). The resulting reaction mixture was heated at 130C for four days. The reaction was cooled to RT, and filtered through a pad of celite with an aid of EtOAc. The filtrate was concentrated and the crude product was dissolved in DCM and chromatographed through a Redi-Sep pre-packed silica gel column (4Og), eluting with a gradient of 10% to 25% to 50% of EtOAc in hexane, to provide 6-chloro-N7-(4-(pyridin-3-yl)pyrimidin-2-yl)-N3-(3- (trifluoromethyl)phenyl)benzo[d]isoxazole-3,7-diamine as off-white solid. Found M+H+ = 483
  • 14
  • [ 1722-12-9 ]
  • [ 483324-01-2 ]
YieldReaction ConditionsOperation in experiment
To a solution of butyllithium (1.6M in hexanes, 9.7 ml, 16 mmol) in 25 ml of anhydrous ether at -78C was added 3-bromopyridine (1.5 ml, 16 mmol) over 5 min. The resulting mixture was stirred at -75C for 1 h. A suspension of 2- chloropyrimidine (1.8 g, 16 mmol) in 15 ml of ether was then added in portions <n="36"/>over 8 min. The resulting suspension was stirred for 30 min at -30C and allowed to warm to O'C for 1 h. The reaction was quenched with water (0.5 ml, 1.5 eq.) in THF (5 ml) and then 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (3.8 g, 17 mmol) in THF (12 ml) was added. The resulting suspension was stirred at RT for 15 min, then cooled to 0C. Hexane (13 nriL) was added followed by 0*C solution of NaOH (12 ml, 3N). The suspension was stirred at 0C for 5 min, 50 ml of water was added and the layers were separated. The organic layer was dried (Na2SO4) and concentrated in vacuo. The crude product was dissolved in DCM and chromatographed through a Redi-Sep pre-packed silica gel column (120 g), eluting with a gradient of 20% to 65% EtOAc in hexane, to provide 2-chloro-4- (pyridin-3-yl)pyrimidine as off-white solid. Found M+H* = 192, 194
  • 15
  • [ 3934-20-1 ]
  • [ 1692-25-7 ]
  • [ 483324-01-2 ]
YieldReaction ConditionsOperation in experiment
74.6% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 4h;Inert atmosphere; Green chemistry; In a 250 mL three-necked flask,2,4-dichloropyrimidine (5.0 g, 33.56 mmol)Dissolved in 1,4-dioxaneAnd water (4: 1, 50 mL) A solution of 3-boronic acid pyridine (4.95 g, 40.27 mmol),Potassium carbonate (9.28 g, 67.12 mmol)And Pd (dppf) Cl2 (2.45 g, 3.36 mmol);The system was replaced with argon three times,Gradually heated to 90 C,Reaction for 4 hours;After the reaction, the system was concentrated under reduced pressure to remove most of the solvent,Ethyl acetate (150 mL)And water (100 mL),Extraction and separation,The aqueous phase was then extracted with ethyl acetate (80 mL)The organic phases were combined,Re-water (80 mL x 2) and saturateWashed with brine (80 mL x 2)Liquid separation,The organic phase was dried over anhydrous sodium sulfate for 3 hours,Filtration and concentration,Crude;The crude product was added petroleum ether (32 mL)And ethyl acetate (6 mL) were stirred for 1 hour,filter,Dried in vacuo to give 4.8 g of 2-chloro-4- (3-pyridyl) pyrimidine,The yield was 74.6%Purity HPLC was greater than 95%.
73% With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; water; for 16h;Heating; Reflux; Inert atmosphere; Example 11 Preparation of 2-chloro-4-(pyridin-3-yl)pyrimidine[00106] Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed a solution of pyridin-3-ylboronic acid (4.42 g, 36.0 mmol, 1.00 equiv) in THF/H2O (30 mL), a solution of 2,4-dichloropyrimidine (5.40 g, 36.2 mmol, 1.00 equiv) in THF/H2O (30 mL), Na2CO3 (11.5 g, 108 mmol, 3.00 equiv) and PdCl2(PPh3)2 (1.80 g, 2.57 mmol, 0.06 equiv). The resulting solution was heated to reflux for 16 hrs in an oil bath. The reaction mixture was cooled and quenched by the addition of 100 mL of water. The resulting solution was extracted with 5x200 mL of ethyl acetate. The organic layers were combined, washed with 3x200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1: 1). This resulted in 5 g (73%) of 2-chloro-4-(pyridin-3-yl)pyrimidine as a yellow solid.
52% With bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; for 14h;Reflux; Inert atmosphere; General procedure: To a solution of 2,4-dichloro-5-methylpyrimidine (500 mg, 3.1 mmol) and 4-trifluoromethoxylphenylboronic acid (644 mg, 3.1 mmol) in dioxane (15 mL), Pd(PPh3)2Cl2 (215 mg, 0.3 mmol) and 2M Na2CO3 (920 mg, 8.7 mmol) were added. The mixture was stirred at reflux for 14 h under N2 atmosphere. The reaction mixture was cooled to room temperature and filtrated. The filtrate was diluted with H2O (100 mL) and then extracted with EtOAc, and the organic layer was dried over anhydrous Na2SO4, After filtration, the filtrate was evaporation and purified by chromatography (petroleum ether/ EtOAc, 5:1) to give the product as oil (700 mg, 73 %).
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water; at 60℃; for 16h; Step 1.Synthesis of 2-chloro-4-(3-pyridyl)pyrimidine nitrogen was bubbled through a solution of 2,4-dichloropyrimidine (1 eq) in tetrahydrofuran and water (3:1) for 0.5 h. bis(diphenylphosphino)ferrocene Palladium(II)chloride (0.05 eq) followed by pyridine-3-boronic acid (1 eq) and sodium carbonate (3 eq) was added and the mixture was heated to 60 C. for 16 h under nitrogen.The reaction mixture was concentrated and partitioned between ethyl acetate and water.The organic layer was washed with brine and dried with sodium sulfate and concentrated.Purification on silica gel gave 2-chloro-4-(3-pyridyl)pyrimidine. MS: MH+=190.
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 100℃; for 1h; 2-Chloro-4-(pyridin-3-yl)pyrimidine: Pyridin-3-ylboronic acid (263 mg, 2.14 mmol), PEPPSI - IPr (132 mg, 0.195 mmol), and potassium carbonate (2.4 ml of 2 M aqueous solution, 4.8 mmol) were added to 2,4-dichloropyrimidine (290 mg, 1 .95 mmol) in 1 ,2- dimethoxyethane (8 mL) . The reaction mixture was stirred at 100 C for 1 h. The solvents were removed under reduced pressure, and the residue was dissolved in DCM and filtered. The filtrate was purified with silica gel chromatography (20% - 60% EtOAc in hexanes) to yield 150 mg, 40.2 % yield of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) delta 1 H NMR (400 MHz, CHLOROFORM-d) delta 9.28 (br. s., 1 H), 8.79 (d, J = 3.92 Hz, 1 H), 8.73 (d, J = 5.09 Hz, 1 H), 8.46 (d, J = 8.03 Hz, 1 H), 7.72 (d, J = 5.29 Hz, 1 H), 7.49 (dd, 1 H). LCMS: tR = 0.47 min, 93%. MS m/z = 192 (M+H)+.

  • 16
  • [ 610-81-1 ]
  • [ 483324-01-2 ]
  • [ 611225-84-4 ]
YieldReaction ConditionsOperation in experiment
In DMF (N,N-dimethyl-formamide); at 150℃; for 0.166667h;Microwave; Step 2.Synthesis of 2-nitro-4-(4-(3-pyridyl)pyrimidin-2-yloxy)phenylamine A solution of 4-amino-3-nitro-phenol (1 eq) and <strong>[483324-01-2]2-chloro-4-(3-pyridyl)pyrimidine</strong> (1 eq) in N,N-dimethylformamide was microwaved at 150 C. for 10 mins.The reaction mixture was partitioned between ethyl acetate and water.The organic layer was concentrated and purified on silica gel to yield 2-nitro-4-(4-(3-pyridyl)pyrimidin-2-yloxy)phenylamine. MS: MH+=309.
  • 18
  • [ 99-55-8 ]
  • [ 483324-01-2 ]
  • [ 152460-09-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In butan-1-ol; for 38h;Heating / reflux; A 250 ml reactor, equipped with a mechanical stirrer and a reflux condenser, was charged with 2-chloro-4-(3-pyridyl)-pyrimidine (0.5 g, 2.6 mmol), 2-amino-4-nitrotoluene (0.5 g, 3.2 mmol), n-butanol (15 ml) and concentrated HCl (5 drops) and the mixture was refluxed for 38 hours. Then, the mixture was cooled, and 6 N NaOH was added to pH 8. The solvent was evaporated under reduced pressure and water (20 ml) was added to the residue, followed by extraction with dichloromethane (2×20 ml). The combined organic phase was concentrated to dryness to give the crude N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-pyrimidine-amine, which was purified by column chromatography to yield a product having 80% purity. The residue was re-slurried twice in methanol (2×2 ml) and in water (3 ml) and dried under reduced pressure
290 g With copper(l) iodide; 2-(dimethylamino)ethyl methacrylate; potassium carbonate; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere; 190 g of 2-chloro-4-(pyridin-3-yl)pyridine under a nitrogen atmosphere,167 g of 2-methyl-5-nitroaniline, 47 g of cuprous iodide,Anhydrous potassium carbonate 276gAnd 22 g of dimethylaminoethyl methacrylate added to 1,4-dioxane solution 2000 mLMedium, heating at 100 C, reaction for 20 h, TLC detection,The raw material is completely reacted; first under reduced pressure,Evaporate most of the solvent dioxane, after cooling to room temperature,The reaction mixture was poured into ice water and a large amount of white solid precipitated.Filtration, a small amount of n-hexane rinse, vacuum dry to pureN-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidinamine 290 g.
  • 19
  • [ 897031-20-8 ]
  • [ 483324-01-2 ]
YieldReaction ConditionsOperation in experiment
65% With thionyl chloride; N,N-dimethyl-formamide; at 70℃; for 6h; (2) Feeding: Weigh 2-oxo-4- (3-pyridyl) - pyrimidine and 1.73g thionyl chloride 20.0ml into the reaction flask and catalyst DMF770muL, system reaction 6h after TLC monitoring material point at 70 disappeared, the reaction was completed.Post-treatment: the system to be cooled, the system was poured into 400ml of ice water, adjusted to pH 8 with sodium hydroxide solution, (30ml × 3) and extracted with ethyl acetate, the extract was dried over anhydrous sodium sulfate, suction filtered, the The filtrate was evaporated to dryness to give a pale yellow solid, yield 65%.
56% With trichlorophosphate; at 50℃; for 4.5h; 2. Preparation of 2-chloro-4-(3-pyridyl)-pyrimidine In a 250 ml two necked flask, equipped with a mechanical stirrer and a condenser, a mixture of 2-oxo-4-(3-pyidyl)-pyrimidine (3 g, 0.017 mol) and POCl3 (18 ml) was stirred at 50 C. for 4.5 hrs. The reaction mixture was poured into cold water (50 ml) and neutralized with 47% aqueous NaOH solution to pH 8. The solution was extracted with ethyl acetate (2*50 ml). The combined ethyl acetate phase was dried over magnesium sulfate and evaporated to dryness to give 2-chloro-4-(3-pyridyl)-pyrimidine in 56% yield, having a purity of 97%.
520 g With trichlorophosphate; In toluene; for 5h;Reflux; In a 5000 mL round bottom flask, add 1300 mL of toluene.Then, 500 g of 4-(pyridinyl-3-yl)pyrimidine-2(H)-one was added and stirred at room temperature for 20 minutes.Slowly add 532g of phosphorus oxychloride, heat to a slight reflux, and stir for 5 hours.After the TLC detection material completely disappeared, the reaction solution was cooled to room temperature.Then the reaction solution was poured into 3,500 mL of ice water.Adding organic solvent to dichloromethane, extracting three times, and combining the organic phases,Then concentrated and separated by column chromatography to obtain pure2-chloro-4-(pyridin-3-yl)pyridine 520g.
  • 20
  • [ 6375-16-2 ]
  • [ 483324-01-2 ]
  • 6-methyl-N'-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% To a solution of N-(3-amino-4-methylphenyl)acetamide (5 g, 25 mmol, commercially available) in DMF (5 mL) was added 2- chloro-4-(pyridin-3-yl)-pyrimidine (4 g, 35 mmol, commercially available) and KI (0.5 g, 3 mmol). After stirring at 100 C overnight, the reaction mixture was cooled to 10 C, quenched with H2O, (10OmL), extracted with CH2C12 (2x100 mL) and the combined organic layers were dried (Na2SO4) and concentrated. The residue was dissolved in cone. HCl (10 mL), stirred at 80 C for 2h, and then concentrated to yield 6-methyl-N'-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-l,3-diamine hydrochloride (4.5 g, 65% yield) as the HCl salt.
  • 21
  • [ 138-39-6 ]
  • [ 483324-01-2 ]
  • [ 1114991-73-9 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 90℃; for 12h; To 0.1 M NMP solution of 1 equiv. of 2-chloro-4-aryl/heteroaryl-pyrimidine is added 1.2 equiv. of 4-aminomethyl-benzenesulfonamide and 5 equiv. of i-Pr2NEt. After heating at 90 C. for 12 h, the reaction is cooled to 23 C. and 10 ml of H2O was added. The mixture is extracted with 3×5 ml of ethyl acetate, and the combined organics are washed with 4×5 ml of H2O, and evaporated to yield an orange viscous oil. Purification by RP-HPLC as outlined in Procedure A, Step 2 gives the title compounds.
  • 22
  • [ 109-01-3 ]
  • [ 483324-01-2 ]
  • [ 682798-27-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In toluene; at 75℃; General procedure: A solution of the corresponding lithium reagent (10 mmol) in THF (10 mL) was stirredat 50 C and treated dropwise with a solution of 2-chloropyrimidine, 2-chloro-5-propylpyrimidine or2-chloroquinazoline (12 mmol) in THF (15 mL). The mixture was allowed to reach 0 C within 2 h, thenquenched with a solution of water in THF (1:5, 6 mL), stirred at 0 C and treated with a solution of DDQ(2.3 g, 10 mmol) in THF (5 mL). After stirring for an additional 10 min at 0 C, the mixture was treatedwith a cold solution of sodium hydroxide (4 M, 5 mL, 20 mmol), stirred and extracted immediatelywith ether/hexanes (1:1, 3 x 10 mL). The combined extracts were dried with anhydrous sodium sulfate,decolorized by filtration through a pad of silica gel (5 g) and concentrated on a rotary evaporator. Theresultant crude 4-substituted 2-chloropyrimidine or 2-chloroquinazoline was treated with a primaryor secondary amine (30 mmol) in toluene (20 mL) in the presence of anhydrous potassium carbonateand the mixture was heated at 75 C for 5-10 h, after which time a TLC analysis on silica gel elutingwith ether/triethylamine (9:1) showed the absence of the substrate. Preparative chromatography wasconducted eluting with ether/triethylamine/hexanes (9:5:5) to give product 1, 2, 21, 23, 24, 26, 29, 30,32, 36-46 (Scheme 1) and 48 (Scheme 2).
  • 23
  • C9H8ClN3 [ No CAS ]
  • [ 483324-01-2 ]
  • 24
  • [ 60573-68-4 ]
  • [ 1722-12-9 ]
  • [ 483324-01-2 ]
YieldReaction ConditionsOperation in experiment
General procedure: A solution of the corresponding lithium reagent (10 mmol) in THF (10 mL) was stirredat 50 C and treated dropwise with a solution of 2-chloropyrimidine, 2-chloro-5-propylpyrimidine or2-chloroquinazoline (12 mmol) in THF (15 mL). The mixture was allowed to reach 0 C within 2 h, thenquenched with a solution of water in THF (1:5, 6 mL), stirred at 0 C and treated with a solution of DDQ(2.3 g, 10 mmol) in THF (5 mL). After stirring for an additional 10 min at 0 C, the mixture was treatedwith a cold solution of sodium hydroxide (4 M, 5 mL, 20 mmol), stirred and extracted immediatelywith ether/hexanes (1:1, 3 x 10 mL). The combined extracts were dried with anhydrous sodium sulfate,decolorized by filtration through a pad of silica gel (5 g) and concentrated on a rotary evaporator. Theresultant crude 4-substituted 2-chloropyrimidine or 2-chloroquinazoline was treated with a primaryor secondary amine (30 mmol) in toluene (20 mL) in the presence of anhydrous potassium carbonateand the mixture was heated at 75 C for 5-10 h, after which time a TLC analysis on silica gel elutingwith ether/triethylamine (9:1) showed the absence of the substrate. Preparative chromatography wasconducted eluting with ether/triethylamine/hexanes (9:5:5) to give product 1, 2, 21, 23, 24, 26, 29, 30,32, 36-46 (Scheme 1) and 48 (Scheme 2).
  • 25
  • [ 483324-01-2 ]
  • [ 1262215-65-5 ]
  • 26
  • [ 483324-01-2 ]
  • [ 1262215-41-7 ]
  • 27
  • [ 483324-01-2 ]
  • [ 1262215-43-9 ]
  • 28
  • [ 1262215-61-1 ]
  • [ 483324-01-2 ]
  • [ 1262215-63-3 ]
YieldReaction ConditionsOperation in experiment
23% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); XPhos; In 1,4-dioxane; for 18h;Heating; Reflux; Inert atmosphere; Example 12 Preparation of ethyl A^-(3-fluoro-4-methyl-5-(4-(pyridin-3-yl)pyrimidin- 2-ylamino)phenyl)carbamate[00107] Into a 100-mL 3 -necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed a solution of ethyl N-(3-amino-5-fluoro-4- methylphenyl)carbamate (1.00 g, 4.72 mmol, 1.00 equiv) in 1,4-dioxane (20 mL), 2- chloro-4-(pyridin-3-yl)pyrimidine (500 mg, 2.62 mmol, 0.55 equiv), K2CO3 (1.3 g), Pd(PPh3)4Cl2 (0.1 g) and X-Phos (0.1 g). The resulting solution was heated to reflux for 18 hrs in an oil bath. The reaction mixture was cooled and concentrated under vacuum. The residue was diluted with water and extracted with 2x100 mL of ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:2). This resulted in 0.42 g (23%) of ethyl N-(3-fluoro-4- methyl-5-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)carbamate as a pale yellow solid.
  • 29
  • [ 510771-81-0 ]
  • [ 483324-01-2 ]
  • [ 1433205-40-3 ]
YieldReaction ConditionsOperation in experiment
17.95% With N,N-dimethyl acetamide; triethylamine; at 160℃; for 0.166667h;Microwave irradiation; 4-(Pyridin-3-yl)-A -(4-(5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)benzyl)pyrimidin-2- amine, trifluroacetic acid salt: To a suspension of 4-(5-(trifluoromethyl)-1 ,2,4-oxadiazol- 3-yl)phenyl)methanamine (70 mg, 0.29 mmol), <strong>[483324-01-2]2-chloro-4-(pyridin-3-yl)pyrimidine</strong> (50 mg, 0.26 mmol) in A/JV-dimethylacetamide (2.5 ml.) was added a solution of Et3N (0.091 ml_, 0.652 mmol) in one charge. The reaction vessel was sealed and heated to 160 C under microwave irradiation for 10 min. After cooling the reaction, the solvent was removed under reduced pressure, and the mixture was dissolved in MeOH and purified via reverse phase prep-HPLC (10% - 100% MeCN in water with TFA 0.05%) to give a solid. The solid obtained was triturated with Et20 to provide the title compound (24 mg, 0.047 mmol, 17.95 % yield) as a white powder. 1H NMR (400 MHz, METHANOL-^) delta ppm 9.31 (br. s., 1 H), 8.76 (d, J = 5.1 Hz, 2 H), 8.45 (d, J = 5.3 Hz, 1 H), 8.09 (d, J = 8.2 Hz, 2 H), 7.74 - 7.89 (m, 1 H), 7.62 (d, J = 8.0 Hz, 2 H), 7.30 (d, J = 5.3 Hz, 1 H), 4.80 (s, 2 H). LCMS: tR, = 0.82 min, 98%. MS m/z = 399 (M+H)+.
  • 30
  • [ 483324-01-2 ]
  • N-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,4-diamine [ No CAS ]
  • 31
  • [ 483324-01-2 ]
  • C22H16N6O3 [ No CAS ]
  • 32
  • [ 483324-01-2 ]
  • [ 1437315-22-4 ]
  • 33
  • [ 483324-01-2 ]
  • JNK-IN-7 [ No CAS ]
 

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