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Chemical Structure| 49845-33-2 Chemical Structure| 49845-33-2
Chemical Structure| 49845-33-2

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CAS No.: 49845-33-2

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Product Details of [ 49845-33-2 ]

CAS No. :49845-33-2
Formula : C4HCl2N3O2
M.W : 193.98
SMILES Code : C1=C(C(=NC(=N1)Cl)Cl)[N+](=O)[O-]
MDL No. :MFCD00127867
InChI Key :INUSQTPGSHFGHM-UHFFFAOYSA-N
Pubchem ID :521266

Safety of [ 49845-33-2 ]

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

Calculated chemistry of [ 49845-33-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 40.87
TPSA ?

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

71.6 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

1.0
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

1.95
Log Po/w (WLOGP)?

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

1.69
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.

-0.29
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

0.28
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.93

Water Solubility

Log S (ESOL):?

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

-2.61
Solubility 0.477 mg/ml ; 0.00246 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.

-3.08
Solubility 0.162 mg/ml ; 0.000835 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

-2.27
Solubility 1.04 mg/ml ; 0.00538 mol/l
Class?

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

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.

-6.1 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

 2.0
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

2.0 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)

 2.0

Application In Synthesis of [ 49845-33-2 ]

* 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 [ 49845-33-2 ]

[ 49845-33-2 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 49845-33-2 ]
  • [ 1920-66-7 ]
YieldReaction ConditionsOperation in experiment
92.6% With ammonium hydroxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 1h; To a solution of NH3.H2O (aq., 24 mL) and DIPEA (37.2 mL) in DCM (400 mL) was added dropwise a solution of compound 21-1 (30 g, 15436 mmol) in DCM at 0 C., and the reaction solution was stirred at 0 C. for 1 h, followed by filtration. The filter cake was dried to give compound 21-2 (25 g, Yield 92.6%) as yellow solid. LCMS (ESI) m/z: 175.0 (M+1)
90.1% With ammonia; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; at 0℃; for 1h; Aqueous ammonia(8.0ml) and N,N-diisopropylethylamine(13.2ml) were dissolved into 150ml dichloromethane. The mixture was added dropwise to a solution of 2,4-dichloro-5-nitropyrimidine(10.0g) in dichloromethane(30ml) at 0C. After the completion of the dropwise addition, the mixture was kept at the same temperature to react for 1 hour. The precipitate was filtered off. The filter cake was recrystallized to obtain a yellow solid(8.1g) in a yield of 90.1%. 1H NMR(400 MHz, DMSO-d6): delta 9.20(s, 1H), 9.02(s, 1H), 8.60(s, 1H)ppm.
90% With ammonia; In methanol; dichloromethane; at 0℃; for 1.5h; General procedure: Commercial 1a (50mmol) was dissolved in dichloromethane (80mL), mixture was cooled to 0C, solution of NH3 in MeOH (4mol/L, 12.5mL) was added by dripping slowly, after 30min, the mixture maintained at 0C for 1h. The reaction mixture was filtered, and the insoluble material was washed with ethyl acetate (20mL) and water (30mL) to get 2a (8.66g), yield 90%. Compound 2a (50mmol) was dissolved in THF (40mL), then absolute ethyl alcohol (20mL), water (20mL), Fe (4eq) and ammonium chloride (2eq) were added. The mixture was refluxed until raw material disappeared. The reaction mixture was filtered and filter liquor was evaporated by reducing pressure to get 3a (2.4g), yield 33%. Compound 3a (17mmol) was dissolved in DMF (30mL), triethylamine (3eq) was added, and acetyl isothiocyanate (1eq) was added by dripping slowly, the mixture was stirred at room temperature for 30min, then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 1.5eq) was added and stirred overnight at room temperature. Pulled the mixture into ice water, using concentrated HCl regulates pH to 1, the mixture was filtered, the residue was dried and washed by water to give 4a (2.0g), yield 60%. Compound 4a (10mmol), 5a/5b/5c/5d/5e (1.2eq), 120mL 1,4-dioxane, 10mL water, Pd(dppf)Cl2 (0.1eq), and NaHCO3 (1eq) were added to a round-bottomed flask, mixture was stirred for 12h at 90C. Solvent was removed by reduced pressure distillation, residue was purified by preparative HPLC (MeCN+0.05% TFA, H2O 0.1%+TFA), Ta-e were finally obtained from above steps, yield 0.58-5.5%.
89% With ammonia; In ethanol; dichloromethane; at 0℃; A solution of 2,4-dichloro-5-nitropyrimidine (14) (0.90 g, 4.64 mmol)in DCM (6.7 mL, 0.7 M) was added dropwise to a solution of 2 MAmmonia in EtOH (6 mL) stirring at 0 C. The reaction was stirred for30 min at 0 C, after which the mixture was warmed to RT and the solventremoved in vacuo.40 The crude residue was purified via silica gel chromatography(4:1 Hexanes:EtOAc) to afford the desired compound as ayellow solid (2.40 g, 13.8 mmol, 89%). Rf 0.24 (4:1 Hexanes:EtOAc); M.p.212-213 C (Lit.=220-221)41; IR (cm-1) 3430, 3056, 1642, 1579, 1534;1H NMR (400 MHz, DMSO-d6) 8.58 (1H, s, NH2), 9.02 (1H, s, H-6), 9.19(1H, s, NH2); 13C NMR (100 MHz, DMSO-d6) delta 127.0 (Ar-C), 157.5 (Ar-C),158.0 (Ar-C), 162.6 (Ar-C); HRMS cal. C4H2ClN4O2 (ES-) m/z 172.986629[M-H]-, found 172.988897.
84% With ammonium hydroxide; sodium hydroxide; In tetrahydrofuran; at 55℃; for 2h; To 2,4-dichloro-5-nitropyrimidine (500 mg, 2.5 mmol) dissolved in tetrahydrofuran (10 mL), sodium hydroxide (238 mg, 2.8 mmol) and aqueous ammonia (0.3 mL) was added, and reacted for 2 hrs at 55C. The solvent was removed under reduced pressure, and the residue was separated by flash column chromatography (dichloromethane: methanol=100:1), to obtain Compound w: 2-chloro-5-nitro-4-aminopyrimidine as a white solid (0.47 g, yield 84%). MS(ESI)m/z: [M+H]+=175.
With ammonia; In water; ethyl acetate; at 20℃; for 1h; To a solution of 5 g (25 mmol) 2,4-dichloro-5-nitro-pyrimdine in 150 mL EtOAc was added 50 mL 28-34% aqueous NH4OH. After stirred at rt for 1 hour, the reaction mixture was filtered. The organic layer was concentrated to give desired solid product. 1H NMR (CD3OD): 9.03 (1H, s). LC-MS [M+H]=175.
With ammonia; In water; at 0℃; for 0.5h; To a rapidly stirred solution of saturated aqueous ammonium hydroxide (50 mL) and ice in a 0 deg. C. bath was added 2,4-dichloro-5-nitropyrimidine (6.0 g, 31 mmol) in portions. The resulting yellow foamy mixture was allowed to stir for 30 min, at which point the precipitate was isolated by filtration. The solid was rinsed several times with ice-cold water and once with ice cold ethanol to give a peach-colored solid. The crude solid was purified by adsorption onto 18 g silica gel, followed by silica gel chromatography, eluding with 0-20% MeOH/dichloromethane to give 2-chloro-5-nitropyrimidin-4-amine as an off-white solid. MS (ES+): 175 (M+H)+; Calc. for C4H3ClN4O2=174.55.
With ammonia; In ethanol; dichloromethane; at 0℃; for 0.333333h; (1) To a solution of 2,4-dichloro-5-nitropyrimidine (50 g) in dichloromethane (400 ml) was added dropwise 2 mol/L ammonia/ethanol solution (387 mL) at 0 C. and the mixture was stirred at the same temperature for 20 minutes. The crystals precipitated were collected by filtration and was washed with ethyl acetate (100 ml) and water (150 ml), and was then dried to give 2-chloro-5-nitropyrimidin-4-amine 42 g. 1H-NMR (DMSO-d6) delta: 8.59 (1H, br s), 9.02 (1H, s), 9.19 (1H, br s).

  • 2
  • [ 7664-41-7 ]
  • [ 49845-33-2 ]
  • [ 1920-66-7 ]
  • 3
  • [ 21911-84-2 ]
  • [ 49845-33-2 ]
  • [ 1001346-30-0 ]
YieldReaction ConditionsOperation in experiment
100% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 18 - 25℃; To a solution of; 3,4-dichloro-5-nitropyrimidine (Aldrich; 12.59 g, 64.9 mmol) in anhydrous THF (300 mL) at room temperature under a nitrogen atmosphere was added dropwise over 6 hrs a solution of Methyl3-anilinopropanoate (Intermediate 106; 12.795 g, 71.39 mmol) and Hunigs base (13.54 mL, 77.88 mmol) in anhydrous THF (300 mL) The reaction mixture was stirred over night at room temperature.The solvent was evaporated at 40 C. and the residue dissolved in DCM and washed with water and saturated brine. The resulting organic phase was dried over anhydrous sodium sulphate then pre-absorbed onto silica and purified by vacuum filtration chromatography eluting with dichloromethane. Evaporation of product containing fractions afforded the title compound as a dark red oil (24.25 g, >100%)MS m/z 275 [M+H]+. Retention time 2.32 mins
91% With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 50℃; for 1h; A mixture of <strong>[21911-84-2]methyl 3-(phenylamino)propanoate</strong> (1.42 g, 7.93 mmol), DIEA (2.76 mL, 15.86 mmol) and 2,4-dichloro-5-nitropyrimidine (2.30 g, 1 1.90 mmol) in dioxane (40 mL) was heated at 50 C for Ih. After the reaction was complete as monitored by TLC, the reaction solution was concentrated in vacuo and the residue was purified by silica-gel column chromatography with ethyl acetae and hexane (1/20, v/v) to give the title compound III-1-a (2.5 g, 91%), MS (ESI) m/z 337 (M+H)+.
  • 4
  • [ 157837-31-5 ]
  • [ 49845-33-2 ]
  • [ 840537-54-4 ]
YieldReaction ConditionsOperation in experiment
With N,N-diethylaniline; In dichloromethane; at -40 - 20℃; A mixture of 2, 4-DICHLORO-5-NITROPYRIMIDINE (5 mmol) in CH2C12 (20 ml) was stirred at -30 C/-40 C. ALTERNATELY, a solution of 3- (5-OXAZOLYL)-BENZENAMINE (5 mmol) in CH2C12 (10 ml) and a solution OF N, N-DIETHYLBENZENAMINE (5 mmol) in CH2C . 2 (10 ML) were added dropwise over a period of 1 hour, followed by stirring for 2 hours at-20 C/-30 C. The mixture was allowed to come to room temperature while stirring. The mixture was diluted with 50 ml of CH2CL2 and 50 ml of ice water was added. The precipitate was filtered and dried. Yield : 490 mg of intermediate 51. Of the filtrate, the layers were separated and the organic layer was dried, filtered and evaporated. The residue was stirred in CH3CN. The precipitate was filtered off and dried. Yield : 305 mg of intermediate 51.
With N,N-diethylaniline; In dichloromethane; at -40 - -20℃; for 3h; A mixture of 2,4-dichloro-5-nitropyrimidine (5 mmol) in CH2Cl2 (20 ml) was stirred at - 30C/-40C. Alternately, a solution of <strong>[157837-31-5]3-(5-oxazolyl)-benzenamine</strong> (5 mmol) in CH2Cl2 (10 ml) and a solution of N,N-diethylbenzenamine (5 mmol) in CH2Cl2 (10 ml) were added dropwise over a period of 1 hour, followed by stirring for 2 hours at- 20C/-30C. The mixture was allowed to come to room temperature while stirring. The mixture was diluted with 50 ml of CH2Cl2 and 50 ml of ice water was added. The precipitate was filtered and dried. Yield: 490 mg of intermediate 41. Of the filtrate, the layers were separated and the organic layer was dried, filtered and evaporated. The residue was stirred in CH3CN. The precipitate was filtered off and dried. Yield: 305 mg of intermediate 41.
  • 5
  • [ 140645-24-5 ]
  • [ 49845-33-2 ]
  • [ 1021693-28-6 ]
YieldReaction ConditionsOperation in experiment
75 - 83% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -78℃; for 2h; (S)-tert-butyl 3-((2-chloro-5-nitropyrimidin-4-ylamino)methyl) piperidine-1-carboxylate (12)[0074] To 1.267 g (6.53 mmol, 1.0 equiv.) of 2,4-dichloro-5-nitropyrimidine (Toronto Research Chemicals) in 8 mL of anhydrous THF at -78 0C was added dropwise a solution of 6.53 mmol (1 equiv.) of an amine and 1.25 mL of JV,iV-diisopropylethylamine in 6.5 mL anhydrous THF.[0075] The reaction mixture was stirred for 30 min at -78 0C and then allowed to warm to 25 0C and stirred for an additional 1 h. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel. EPO <DP n="35"/>[0076] (S)-tert-butyl 3-((2-chloro-5-nitropyrimidin-4-ylamino)methyl) piperidine- 1- carboxylate (12):[0077] was synthesized using the procedure described above, using (S)-l-Boc-3- (aminomethyl) piperidine (1.4 g, 6.53 mmol, CNH Technologies) as the amine. Purification was performed on silica gel, using a 6 / 1 mixture of hexanes / ethyl acetate as the mobile phase. The desired product was obtained as a yellow solid (1.90 g) in 78 % yield. 1H NMR (300 MHz, CDCl3), ppm: 9.05 (s, IH), 8.56 (br s, IH), 3.85 (dd, 2H), 3.59 (m, 2H), 3.03 (br t, IH), 2.87 (dd, IH), 1.86 (m, 2H), 1.69 (m, IH), 1.46 (s, 9H), 1.40 (m, 2H, overlapping with 1.46 ppm).
  • 6
  • [ 33024-60-1 ]
  • [ 49845-33-2 ]
  • [ 899806-21-4 ]
YieldReaction ConditionsOperation in experiment
93% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78℃; for 2.25h;Inert atmosphere; PREPARATION 2 2-Chloro-9-(tetrahydro-2H-pyran-4-yl)-7,9-dihydro-8H-purin-8-one [Show Image]a) 2-Chloro-5-nitro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine Diisopropylethylamine (19.80 mL, 110 mmol) was added dropwise over 15 minutes to a stirred suspension of 2,4-dichloro-5-nitropyrimidine (11.56 g, 60 mmol) and <strong>[33024-60-1]tetrahydro-2H-pyran-4-amine hydrochloride</strong> (WO200424728 A2) (7.81 g, 60 mmol) in dichloromethane (400 mL) at -78 °C under a nitrogen atmosphere. The reaction mixture was stirred at -78 °C for 2 hours and then was allowed to warm to ambient temperature. The solvent was evaporated, water was added and the resultant solid was filtered, washed with water and dried to yield the title compound (13.62 g, 93percent) as a yellow solid. LRMS (m/z): 259 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm 1.62 - 1.80 (m, 2H), 2.06 (d, 2H), 3.59 (t, 2H), 4.04 (d, 2H), 4.45 (td, 1H), 8.33 (br s, 1H), 9.07 (s, 1H).
93% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78℃; for 2.25h;Inert atmosphere; PREPARATION 2 2-Chloro-9-(tetrahydro-2H-pyran-4-yl)-7,9-dihydro-8H-purin-8-one a) 2-Chloro-5-nitro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine Diisopropylethylamine (19.80 mL, 110 mmol) was added dropwise over 15 minutes to a stirred suspension of 2,4-dichloro-5-nitropyrimidine (11.56 g, 60 mmol) and <strong>[33024-60-1]tetrahydro-2H-pyran-4-amine hydrochloride</strong> (WO200424728 A2) (7.81 g, 60 mmol) in dichloromethane (400 mL) at -78 °C under a nitrogen atmosphere. The reaction mixture was stirred at -78 °C for 2 hours and then was allowed to warm to ambient temperature. The solvent was evaporated, water was added and the resultant solid was filtered, washed with water and dried to yield the title compound (13.62 g, 93percent) as a yellow solid. LRMS (m/z): 259 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm 1.62 - 1.80 (m, 2H), 2.06 (d, 2H), 3.59 (t, 2H), 4.04 (d, 2H), 4.45 (td, 1H), 8.33 (br s, 1H), 9.07 (s, 1H).
93% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20℃;Inert atmosphere; a)2-Chloro-5-nitro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amineDiisopropylethylamine (19.80 mL, 110 mmol) was added dropwise over 15 minutes to a stirred suspension of 2,4-dichloro-5-nitropyrimidine (11.56 g, 60 mmol) and <strong>[33024-60-1]tetrahydro-2H-pyran-4-amine hydrochloride</strong> (prepared as described in ), 7.81 g, 60 mmol) in dichloromethane (400 mL) at -78 oC under a nitrogen atmosphere.The reaction mixture was stirred at -78 oC for 2 hours and then was allowed to warm to ambient temperature.The solvent was evaporated, water was added and the resultant solid was filtered, washed with water and dried to yield the title compound (13.62 g, 93percent) as a yellow solid.LRMS (m/z): 259 (M+1)+.1H NMR delta (300 MHz, CDCl3): 1.62-1.80 (m, 2H), 2.06 (d, 2H), 3.59 (t, 2H), 4.04 (d, 2H), 4.45 (td, 1 H), 8.33 (br s, 1 H), 9.07 (s, 1 H).
93% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78℃; for 2.25h;Inert atmosphere; PREPARATION 12-Chloro-9-(tetrahydro-2H^yran-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl}-7,9- dihydro-8H-purin-8-one a) 2-Chloro-5-nitro-yV-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amineLambda/,Lambda/'-Diisopropylethylamine (19.80 ml_, 1 10 mmol) was added dropwise over 15 minutes to a stirred suspension of 2,4-dichloro-5-nitropyrimidine (1 1.56 g, 60 mmol) and tetrahydro-2/-/-pyran-4-amine hydrochloride (prepared as described in WO200424728(A2), 7.81 g, 60 mmol) in dichloromethane (400 mL) at -78 °C under a nitrogen atmosphere. The reaction mixture was stirred at -78 °C for 2 hours and then was allowed to warm to ambient temperature. The solvent was evaporated, water was added and the resultant solid was filtered, washed with water and dried to yield the title compound (13.62 g, 93percent) as a yellow solid.LRMS (m/z): 259 (M+1 )+.1H NMR delta (300 MHz, CDCI3): 1 .62-1 .80 (m, 2H), 2.06 (d, 2H), 3.59 (t, 2H), 4.04 (d, 2H), 4.45 (td, 1 H), 8.33 (br s, 1 H), 9.07 (s, 1 H). b)

  • 7
  • [ 67-63-0 ]
  • [ 49845-33-2 ]
  • [ 1445894-94-9 ]
  • 8
  • [ 1094227-86-7 ]
  • [ 49845-33-2 ]
  • [ 1521197-42-1 ]
YieldReaction ConditionsOperation in experiment
79% With hydrogenchloride; In 1,4-dioxane; water; at 60.0℃; for 90.0h; A mixture of <strong>[1094227-86-7]ethyl 2-(cyclopentylamino)benzoate</strong> (1.40g, 6.0mmol), 4N HCl in dioxane solution (2.25mL, 9.0mmol) and 2,4-dichloro-5-nitropyrimidine (1.74g, 9.0mmol) in dioxane (40mL) was heated at 60C for 90h. After the reaction was complete as monitored by thin layer chromatography (TLC), the reaction solution was concentrated and the residue was purified by silica-gel column chromatography with ethyl acetate and hexane (1/20, v/v) to give the amination product 2 (1.84g, 79%).
79% With hydrogenchloride; In 1,4-dioxane; at 60.0℃; for 90.0h; A mixture of <strong>[1094227-86-7]ethyl 2-(cyclopentylamino)benzoate</strong> (1.40 g, 6.0 mmol), 4 N HCl in dioxane solution (2.25 mL, 9.0 mmol) and 2,4-dichloro-5-nitropyrimidine (1.74 g, 9.0 mmol) in dioxane (40 mL) was heated at 60 C. for 90 hours. After the reaction was complete as monitored by thin layer chromatography (TLC), the reaction solution was concentrated and the residue was purified by silica-gel column chromatography with ethyl acetate and hexane (1/20, v/v) to give the amination product 12 (1.84 g, 79%). MS (ESI) m/z 391 (M+H)+.
  • 9
  • [ 99071-54-2 ]
  • [ 49845-33-2 ]
  • 2-chloro-5-nitro-N-[(quinolin-6-yl)methyl]pyrimidin-4-amine [ No CAS ]
  • 10
  • [ 1376676-65-1 ]
  • [ 49845-33-2 ]
  • C14H13ClN6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With N-ethyl-N,N-diisopropylamine; In toluene; at 40℃; 2,4-Dichloro-5-nitropyrimidine 5.0 g, compound of formula 2 (0.95 eq), diisopropylethylamine and 100 mL at room temperature toluene was added to the reaction flask, heated, and reacted at 40C for 4-6 hours. TLC was controlled and the reaction was completed.Wash with saturated saline,Dry with anhydrous sodium sulfate, concentrate under reduced pressure, cool to 0-5 C, add methyl tert-butyl ether under stirring, precipitate solid, continue stirring at this temperature for 30 minutes, filter and drain to obtain The compound of formula 3 has a yield of 92%.
  • 11
  • [ 186663-74-1 ]
  • [ 49845-33-2 ]
  • tert-butyl (2-((2-chloro-5-nitropyrimidin-4-yl)oxy)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
36.6% With triethylamine; In tetrahydrofuran; at -20℃; for 4h; To a stirred solution of 2,4-dichloro-5-nitropyrimidine (1a) (720 mg, 3.73 mmol)dissolved in THF (20 mL) at -20 C was added TEA (0.78 mL, 5.74 mmol) and<strong>[186663-74-1]tert-butyl (2-hydroxyphenyl)carbamate</strong> (600 mg, 2.87 mmol) dropwise. After stirringat -20 C for 4 h, the reaction mixture was washed with saturated brine (20 mL), water(20 mL×2), and then dried over anhydrous magnesium sulfate. The crude product waspurified by silica gel column chromatography (petroleum ether/ethyl acetate = 40:1)to afford the title compound 2b? as a light yellow powder (417 mg, 36.6%); mp164-166 C; 1H NMR (300 MHz, Acetone-d6) delta (ppm) 10.33 (brs, 1H), 9.24 (s, 1H),8.13-8.08 (m, 1H), 7.43-7.38 (m, 3H), 1.52 (s, 9H); HRMS (ESI): m/z, Calcd. forC15H16O5N4Cl [M+H]+: 367.0804, Found 367.0794.
 

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