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[ CAS No. 1445-39-2 ] {[proInfo.proName]}

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Chemical Structure| 1445-39-2
Chemical Structure| 1445-39-2
Structure of 1445-39-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 1445-39-2 ]

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Product Details of [ 1445-39-2 ]

CAS No. :1445-39-2 MDL No. :MFCD01075666
Formula : C4H4IN3 Boiling Point : -
Linear Structure Formula :- InChI Key :HAFKCGZQRIIADX-UHFFFAOYSA-N
M.W : 221.00 Pubchem ID :241102
Synonyms :

Calculated chemistry of [ 1445-39-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.15
TPSA : 51.8 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.24
Log Po/w (XLOGP3) : 0.51
Log Po/w (WLOGP) : 0.67
Log Po/w (MLOGP) : 0.33
Log Po/w (SILICOS-IT) : 1.31
Consensus Log Po/w : 0.81

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.09
Solubility : 1.81 mg/ml ; 0.00819 mol/l
Class : Soluble
Log S (Ali) : -1.17
Solubility : 15.0 mg/ml ; 0.0679 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.25
Solubility : 1.24 mg/ml ; 0.00561 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.91

Safety of [ 1445-39-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1445-39-2 ]

* 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 [ 1445-39-2 ]

[ 1445-39-2 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 109-12-6 ]
  • [ 1445-39-2 ]
YieldReaction ConditionsOperation in experiment
22.2% With sulfuric acid; iodine; acetic acid; periodic acid; In water; at 80℃; for 24h;Inert atmosphere; Mixture of 2-aminopyrimidine (2.4 g, 25 mmol, 1.0 eq.) and elemental iodine (2.7 g, 10.7 mmol, 0.43eq.) was added to 60 ml of glacial acetic acid, and then added periodic acid (0.86 g, 3.76 mmol, 0.15 eq.) and 0.5 ml concentrated sulfuric acid dissolved in sulfuric acid solution 3 ml of water. Place reactions in a nitrogen atmosphere , the reaction was heated to 80 C for 24 hours. The reaction was then poured into a saturated aqueous solution of sodium thiosulfate in until a clear solution, (200 ml × 3) and extracted with dichloromethane, the combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure, after column chromatography silica gel to give a white solid 2-amino-5-iodopyrimidine (1.4 g, yield 22.2%).
0.4 g With iodine; In dimethyl sulfoxide; at 120℃; for 1h; To a solution of pyrimidin-2-amine (1.0 g, 0.010 mol) in DMSO (10 mL) was added iodine (3.2 g, 0.012 mol). The reaction mixture was stirred at 120C for 1 h. The reaction mass was quenched in water and excess of iodine was neutralised with sodium metabisulphate. The reaction mass was extracted with ethyl acetate and concentrated to afford 0.400 g of the desired product.
  • 2
  • [ 1445-39-2 ]
  • [ 98-09-9 ]
  • [ 90841-92-2 ]
  • 3
  • [ 1445-39-2 ]
  • [ 153400-52-3 ]
  • exo-2-(2-aminopyrimidin-5-yl)-7-carbomethoxy-7-azabicyclo<2.2.1>heptane [ No CAS ]
  • 4
  • [ 109-12-6 ]
  • [ 1600-27-7 ]
  • [ 7732-18-5 ]
  • [ 1445-39-2 ]
  • 5
  • [ 1445-39-2 ]
  • copper (II)-thiophenolate [ No CAS ]
  • 5-phenylsulfanyl-pyrimidin-2-ylamine [ No CAS ]
  • 6
  • [ 1445-39-2 ]
  • potassium-<4-nitro-thiophenolate> [ No CAS ]
  • [ 874494-43-6 ]
  • 7
  • [ 1445-39-2 ]
  • [ 130277-32-6 ]
  • [ 307303-59-9 ]
  • 8
  • [ 1445-39-2 ]
  • 2-fluoro-5-iodopyrimidine [ No CAS ]
  • 9
  • [ 1445-39-2 ]
  • [ 103-63-9 ]
  • 5-phenethyl-pyrimidin-2-ylamine [ No CAS ]
  • 10
  • [ 142-08-5 ]
  • [ 1445-39-2 ]
  • 1-(2-amino-pyrimidin-5-yl)-1<i>H</i>-pyridin-2-one [ No CAS ]
  • 11
  • [ 1445-39-2 ]
  • [ 1066-54-2 ]
  • [ 857265-74-8 ]
YieldReaction ConditionsOperation in experiment
Example 3Synthesis of 5-ethynylpyrimidin-2-amine A flask was charged with <strong>[1445-39-2]5-iodopyrimidin-2-amine</strong> (25.0 g, 110 mmol), acetonitrile (900 ml, 110 mmol), trimethylsilylacetylene (35 ml, 241 mmol), triethylami?e (93 ml, 658 mmol), Pd(PPh3)4CI2 (3.9 g, 5.5 mmol) and finally copper(l) iodide (1.1 g, 5.5 mmol). The flask was put under vacuum then filled with argon and stirred at RT overnight using a mechanical stirrer. The solvent was removed under vacuum, the residue taken up in methanol (600ml) and potassium carbonate (152 g, 1097 mmol) was added. The mixture was stirred at RT using mechanical stirring for 2 hrs. Activated carbon (~50ml_) was added to the reaction and stirring continued for 15min. The reaction mixture was then filtered through a plug of celite and the filtrate was concentrated to a volume of ~400mL and the precipitate was filtered. The filtrate was concentrated down to a thick paste which was slurried in ~150mL of 10%MeOH/H2O for 20 min at RT. The solids were then filtered off to afford 5-ethynylpyrimidin-2-amine.
  • 12
  • [ 1445-39-2 ]
  • [ 108-24-7 ]
  • [ 849236-67-5 ]
YieldReaction ConditionsOperation in experiment
23% With pyridine; at 110℃; for 48h; Step 1: N- (5-LODOPYRIMIDIN-2-YL) acetamide (248) [0400] 5-lodo-pyrimidin-2-ylamine (17,1. 1 g, 4.98 MMOL) and acetic anhydride (14.94 MMOL, 1.41 mL) were dissolved in pyridine (20 mL) and stirred at 110C for 48 hours. The reaction mixture was cooled and quenched with water (50 mL). Ethyl acetate (100 mL) was added and the resulting white precipitate was collected by filtration to afford title compound 248 as a white solid (300 mg, 23% yield NMR: (DMSO) 8 10.67 (s, 1H), 8.85 (s, 2H), 2.18 (s, 3H).
  • 13
  • [ 1445-39-2 ]
  • [ 1066-54-2 ]
  • [ 857265-75-9 ]
YieldReaction ConditionsOperation in experiment
100% With N-ethyl-N,N-diisopropylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; In ethyl acetate; at -20 - 20℃; for 6h; Intermediate 5; o 5-[(Trimethylsilyl)ethynyl]pyrimidin-2-aminePdCl2dppf (146 mg) was added to a solution of <strong>[1445-39-2]2-amino-5-iodopyrimidine</strong> (221 mg), trimethylsilylacetylene (491 mg), CuI (57 mg) and DIPEA (259 mg) in EtOAc (5 mL) at -20C under an inert atmosphere. The reaction was allowed to warm to ambient s temperature and stirred for 6 hours. The reaction mixture was diluted with water (10 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated. The crude product was used directly without further purification (191 mg, 100%); 1H NMR (CDCl3) 0.26 (s, 9H), 5.19 (bs, 2H)3 8.39 (s, 2H); MS m/e M^+MeCN 233. o
100% With N-ethyl-N,N-diisopropylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; In ethyl acetate; at -20 - 20℃; for 6h; 5-[(Trimethylsilyl)ethynyl]pyrimidin-2-amine PdCl2dppf (146 mg) was added to a solution of <strong>[1445-39-2]2-amino-5-iodopyrimidine</strong> (221 mg), trimethylsilylacetylene (491 mg), CuI (57 mg) and DIPEA (259 mg) in EtOAc (5 mL) at -20 C. under an inert atmosphere. The reaction was allowed to warm to ambient temperature and stirred for 6 hours. The reaction mixture was diluted with water (10 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated. The crude product was used directly without further purification (191 mg, 100%); 1H NMR (CDCl3) 0.26 (s, 9H), 5.19 (bs, 2H), 8.39 (s, 2H);
100% With N-ethyl-N,N-diisopropylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; In ethyl acetate; at -20 - 20℃; for 6h; PdCl2dppf (146 mg) was added to a solution of <strong>[1445-39-2]2-amino-5-iodopyrimidine</strong> (221 mg), trimethylsilylacetylene (491 mg), Cul (57 mg) and DIPEA (259 mg) in EtOAc (5 mL) at - 20C under an inert atmosphere. The reaction was allowed to warm to ambient temperature and stirred for 6 hours. The reaction mixture was diluted with water (10 mL). The organic layer was separated, dried (MgS04), filtered and concentrated. The crude product was used directly without further purification (191 mg, 100%) ; 'H NMR (CDCl3) ; 0.26 (s, 9H), 5.19 (bs, 2H), 8.39 (s, 2H); MS m/e MH++MeCN 233.
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In acetonitrile; at 20℃; for 3h; Into a IL round bottom flask was placed the 2-amino-5- iodopyrimidine (8.0 g, 36.2 mmol) , acetonitrile (30OmL), triethylamine (3OmL), TMS acetylene (7.68g, 78.2 mmol), palladium dichloro-bis-triphenylphosphine (1.26g, 1.8 mmol), and copper(I) iodide (0.342g, 1.8 mmol) . The vessel was filled with argon gas and allowed to stir at room temperature for 3 hours. The solvent was evaporated and the crude was taken up in methanol (40OmL) . Then excess potassium carbonate (10eq) was added, and the mixture was stirred at room temperature for 1.5 hours. Activated charcoal was added and the mixture was filtered through celite. The filtrate was concentrated under reduced pressure to afford a tan solid, which was added to a solution of 10% methanol in water (20OmL) . The resulting precipitate was isolated by filtration, dried in a vacuum oven to constant mass and afforded the title compound as a tan solid. MS m/z = 120 [M+H]+. CaIc'd for C6H5N3: 119.

  • 14
  • [ 1445-39-2 ]
  • [ 857266-55-8 ]
  • [ 857266-56-9 ]
YieldReaction ConditionsOperation in experiment
86% With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In DMF (N,N-dimethyl-formamide); at 60℃; for 4h; Triethylamine (1.0 mL) was added to a degassed solution of <strong>[1445-39-2]2-amino-5-iodopyrimidine</strong> (275 mg), tert-butyl 3-ethynylphenyl (methyl) carbamate (Intermediate 42) (298 mg) PdCl2 (PPh3) 2 (17 mg) and cuprous iodide (1.25 mg) in DMF (5.0 mL). The mixture was heated to 60C for 4 hours and concentrated in vacuo. Purification by flash chromatography on silica using 0- 10% MeOH in DCM as eluent gave the title compound as a yellow solid (344 mg, 86%). lH NMR (CDCl3) 1.47 (s, 9H), 3.27 (s, 1H), 5.22 (s, br, 2H), 7.23-7. 31 (m, 3H), 7. 39 (s, 1H), 8.45 (s, 2H); MS m/e MH+ 325.
  • 15
  • [ 1445-39-2 ]
  • [ 14235-81-5 ]
  • 5-[(4-aminophenyl)ethynyl]pyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With N,N,N',N'-tetramethylguanidine;copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); In DMF (N,N-dimethyl-formamide); at 60℃; for 2.5h; A mixture of <strong>[1445-39-2]2-amino-5-iodopyrimidine</strong> (1.10 g), 4-ethynylaniline (0.82 g), 1,1, 3,3- tetramethylguanidine (0.81 g), and copper (I) iodide (9.5 mg) in dry DMF (3.0 mL) was stirred and degassed with nitrogen. Tetrakis (triphenylphosphine) palladium (0) (115 mg) was added and the mixture heated at 60 C for 2.5 hours. The solvent was evaporated and the residue was triturated with DCM. The solid formed was filtered off and washed with water then dissolved in 1: 1 DCM/MeOH, filtered then evaporated. The solid obtained was triturated with ether and dried to give the title compound (0.67 g, 63%) ; 'HNMR (DMSO-d6) 5.50 (s, 2H), 6.55 (d, 2H), 6.95 (s, 2H), 7.15 (d, 2H), 8.35 (s, 2H) ; MS m/e MH+ 211.
  • 16
  • [ 1445-39-2 ]
  • [ 149507-26-6 ]
  • [ 890021-33-7 ]
YieldReaction ConditionsOperation in experiment
Example 38; 5-(4-(6,7-Dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-N- phenylpyrimidin-2-amine; Step 1: Preparation of 5- (3-fluoro-4-methoxgammaphengammal) pyrimidin-2- amine; In a 500 mL round bottom flask under N2, 3-fluoro-4- methoxyphenylboronic acid (5.0 g, 29.4 mmol) and 5-iodopyrimidin- 2-amine (5.5 g, 24.9 mmol) were mixed. Toluene (100 mL) , EtOH (40 mL) and H2O (20 mL) were added, followed by the addition of Na2CO3 (3.0 g, 24.2 mmol). A stream of N2 was bubbled through the mixture for 5 min before the catalyst Pd(PPh)4 (0.30 g, 0.26 mmol) was added. The mixture was heated at 80 C under N2 for 20 h whereby it was cooled to RT. A solution of NaOH (5 N, 10 mL) was added to the mixture and stirring was continued for 10 min. The mixture was filtered and the solid was washed with H2O (3 x 10 mL) , followed by a mixture of hexanes - EtOAc (1:1, 30 mL) . The solid was dried in the air to give the title compound. MS (ESI pos. ion) m/z: 220. CaIc'd for C11H10FN3O: 219.08.
  • 17
  • [ 1445-39-2 ]
  • [ 32779-38-7 ]
YieldReaction ConditionsOperation in experiment
31% With tert.-butylnitrite; copper dichloride; In acetonitrile; at 20 - 60℃;Inert atmosphere; Step A. Preparation of 2-chloro-5-iodopyrimidine [00166] To a stirring solution of <strong>[1445-39-2]5-iodopyrimidin-2-amine</strong> (2.21 g, 10.0 mmol) in CH3CN (20 ml) at room temperature under argon was added copper (II) chloride (2.02 g, 15 mmol) and tert-butyi nitrite (1.55 g, 15 mmol). The reaction mixture was placed in a preheated oil bath (60 0C) under Argon. The reaction mixture was cooled to room temperature and 20 ml of ether was added. The resulting insoluble material was filtered and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM (~2 ml) and loaded onto an 80 g ISCO silica gel column which was eluted with a 20 min gradient from 0% to 100% EtOAc/Hexanes. 778 mg (31%) of 2-chloro-5-iodopyrimidine was obtained as an off- white solid. 1H NMR (400 MHz, CDCl3) delta ppm 8.79 (s, 2 H).
28% With sodium hydroxide; sodium nitrate; In hydrogenchloride; water; (d) A suspension of <strong>[1445-39-2]2-amino-5-iodopyrimidine</strong> (40 g) in concentrated hydrochloric acid (150 ml) was treated dropwise at a temperature of 25 to 30 C. with a solution of sodium nitrate (40 g) in water (70 ml). The reaction mixture was stirred at a temperature of 25 to 30 C. for a further 2 hr and then neutralised by the addition of aqueous 20% sodium hydroxide, the temperature of the reaction mixture being maintained at 10 to 20 C. during the neutralisation by external cooling. The neutralised reaction mixture was filtered to remove solids and the solids were washed several times with chloroform. The filtrate was extracted with chloroform and the combined chloroform washings and extracts were dried and the chloroform was removed by distillation under reduced pressure to give crude 2-chloro-5-iodopyrimidine as a pale brown solid (12 g, 28%) with m.p. 125 C. (Reference m.p. 129-130 C. J. Chem. Soc. (C), 1971, 1889).
1.7 g With tert.-butylnitrite; copper dichloride; In acetonitrile; at 70℃; To a solution of <strong>[1445-39-2]5-iodopyrimidin-2-amine</strong> (10.0 g, 0.045 mol) in acetonitrile (150 mL) was added CuCl2 (11.57 g, 0.067 mol) and teri-butyl nitrite (6.99 g, 0.067 mol). The reaction mass was heated at 70C for 5-6 h. The reaction mass was diluted with ether and the solid obtained was filtered off. The obtained product was purified with column chromatography on silica gel eluting with DCM to afford 1.700 g of the desired product
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