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CAS No. : | 4316-98-7 | MDL No. : | MFCD00023270 |
Formula : | C4H5ClN4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VNSFICAUILKARD-UHFFFAOYSA-N |
M.W : | 144.56 | Pubchem ID : | 78010 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 35.85 |
TPSA : | 77.82 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.08 cm/s |
Log Po/w (iLOGP) : | 0.96 |
Log Po/w (XLOGP3) : | 0.14 |
Log Po/w (WLOGP) : | 0.31 |
Log Po/w (MLOGP) : | -0.63 |
Log Po/w (SILICOS-IT) : | 0.28 |
Consensus Log Po/w : | 0.21 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.32 |
Solubility : | 6.95 mg/ml ; 0.0481 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.33 |
Solubility : | 6.75 mg/ml ; 0.0467 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.53 |
Solubility : | 4.3 mg/ml ; 0.0297 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.78 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With ammonia In water at 100℃; for 46 h; | A mixture of 4,6-dichloro-5-aminopyrimidine (Aldrich Chemical Co.) (2.0 g, 12.2 mmol) and concentrated aqueous ammonia (20 ml) was heated to 100 0C in a sealed glass tube with vigorous stirring for 18 hours. The cooled tube was recharged with concentrated aqueous ammonia (8 ml), aggregates were broken up, and the mixture was reheated at 100 0C for a further 28 hours. The mixture was evaporated to dryness and the solids were washed with water (20 ml) and dried to give the EPO <DP n="118"/>product as yellow crystals (1.71 g, 97percent). LC/MS (LCTl): Rt 1.59 [M+H]+ 147, 145. |
97% | at 100℃; for 46 h; | 2C. 5,6-Diamino-4-chloropyrimidine; A mixture of 4,6-dichloro-5-aminopyrimidine (Aldrich Chemical Co.) (2.0 g, 12.2 mmol) and concentrated aqueous ammonia (20 ml) was heated to 100 0C in a sealed glass tube with vigorous stirring for 18 hours. The cooled tube was recharged with concentrated aqueous ammonia (8 ml), aggregates were broken up, and the mixture was reheated at 100 0C for a further 28 hours. The mixture was evaporated to dryness and the solids were washed with water (20 ml) and dried to give the product as yellow crystals (1.71 g, 97percent). LC/MS (LCTl): Rt 1.59 [M+H]+ 147, 145. |
97% | With ammonia In water at 100℃; for 46 h; | EXAMPLE 13; 6-r4-(Aminophenylmethyl)piperidin-1-yll-7,9-dihydropurin-8-one; 13A. 5,6-Diamino-4-chloropyrimidine; A mixture of 4,6-dichloro-5-aminopyrimidine (Aldrich Chemical Co.) (2.0 g, 12.2 mmol) and concentrated aqueous ammonia (20 ml) was heated to 100 0C in a sealed glass tube with vigorous stirring for 18 hours. The cooled tube was recharged with concentrated aqueous ammonia (8 ml), aggregates were broken up, and the mixture was reheated at 100 0C for a further 28 hours. The mixture was evaporated to dryness and the solids were washed with water (20 ml) and dried to give the product as yellow crystals (1.71 g, 97percent). LC/MS (LCT1): R, 1.59 [M+H]+ 147, 145. |
97% | With ammonia In water at 100℃; for 46 h; | EXAMPLE 6; 4-Amino- 1 -r8-oxo-8,9-dihvdro-7H-purin-6-ylVpiperidine-4-carboxylic acid 4- chloro-benzylamide 6A. 5,6-Diamino-4-chloropyrimidine <n="94"/>A mixture of 4,6-dichloro-5-aminopyrimidine (Aldrich Chemical Co.) (2.0 g, 12.2 mmol) and concentrated aqueous ammonia (20 ml) was heated to 100 0C in a sealed glass tube with vigorous stirring for 18 hours. The cooled tube was recharged with concentrated aqueous ammonia (8 ml), aggregates were broken up, and the mixture was reheated at 100 0C for a further 28 hours. The mixture was evaporated to dryness and the solids were washed with water (20 ml) and dried to give the product as yellow crystals (1.71 g, 97percent). LC/MS (LCTl): Rt 1.59 [MH-H]+ 147, 145. |
83% | at 100℃; Sealed tube | Step 1: The suspension of 4,6-dichloropyrimidin-5-amine (1.64 g, 10 mmol) in 5 mL of cone. NH3 in water in sealed tube was stirred at 100 °C overnight. The solid was collected by filtration and dried under vacuum to give the desired product 6-chloropyrimidine-4,5-diamine as a yellow solid (1.2 g, 83percent yield). LC-MS: m/z 145 (M+H)+. |
71% | With ammonia In methanol at 100℃; for 12 h; | Intermediate 42: 6-Chloro-pyrimidine-4,5-diamine To a 7 N solution of ammonia in MeOH (40 mL) was added 4,6-dichloro-pyrimidin-5-ylamine (8.7 g, 53 mmol) and the solution was heated to 100° C. in a sealed tube. After 12 h, the resulting solution was cooled to rt and allowed to stand for 2 h. The colorless crystalline material that resulted was collected by filtration and washed with ice cold MeOH (10 mL) to give the title compound (5.4 g, 71 percent). MS (ESI): mass calcd. for C4H5ClN4, 144.0; m/z found, 145.0 [M+H]+. 1H NMR ((CD3)2SO): 7.64 (s, 1H), 6.70. (s, 2H), 4.93 (s, 2H). |
70% | With ammonia In methanol at 118℃; | A suspension of 5-Amino-4,6-dichloropyrimidine (3 g, 0.02 mol) in ammonia (25 mL, 7N/MeOH, 0.175 mole) was heated at 118° C. overnight (under pressure). The reaction was cooled to 23° C., filtered and washed with ethanol to obtain 1.92 g (70percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | for 4 h; Heating / reflux | 4, [5-DIAMINO-6-HYDROXYPYRIMIDINE] [(1] g) and dimethylaniline [(1] mL) in POC13 (10 [ML)] were heated at reflux under an inert atmosphere for 4 hours. The reaction mixture was concentrated in vacuo, carefully diluted with ice-water and then neutralised with NaHCO3. The product was extracted with EtOAc (4 x 30 mL) and then the organics were dried [(MGS04),] filtered and concentrated in vacuo. The crude product was triturated with DCM to afford the product as a pale grey solid [(168MG, 15percent)] ; [APOS;H] NMR [(CDC13)] 8 4.95 (br s, 2H), [6. 73] (s, 2H), 7.65 (s, 1H); m/e (MH+MeCN) [+ 186.] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | for 0.833333 h; Reflux; Inert atmosphere | Preparation 131 6-Chloro-7,9-dihydro-purin-8-one Combine 6-chloro-pyrimidine-4,5-diamine (7.46 mmol; 1.08 g); 1,1'-carbonyldiimidazole (2 equiv; 14.92 mmol; 2.42 g) and 1,4-dioxane (20 mL) and heat to reflux under nitrogen for 50 min. Evaporate the yellow solution to an oil. Add DCM (80 mL), let sit 1 h, filter and dry in vacuum oven at 45° C. to provide the title compound (1.22 g; 7.15 mmol; 96percent) MS (ES+): m/z=169 (M-H). |
86% | for 48 h; Heating / reflux | 2D. 6-Chloro-7,9-dihydropurin-8-one; A mixture of the 5,6-diamino-4-chloropyrimidine of Example 6A (1.0 g, 6.92 mmol) and N,N'-carbonyldiimidazole (2.13 g, 13.2 mmol) in 1,4-dioxane (20 ml) was refluxed under <n="119"/>argon for 48 hours. The solution was concentrated to a brown oil, which was triturated and washed with dichloromethane to give an off-white solid (1.02 g, 86percent) LC/MS (LCTl): Rt 2.45 [M+H]+ 173, 171. |
86% | for 48 h; Heating / reflux | 13B. 6-Chloro-7,9-dihydropurin-8-one <n="118"/>A mixture of the 5,6-diamino-4-chloropyrimidine of Example 13A (1.0 g, 6.92 mmol) and N,N'-carbonyldiimidazole (2.13 g, 13.2 mmol) in 1,4-dioxane (20 ml) was refluxed under argon for 48 hours. The solution was concentrated to a brown oil, which was triturated and washed with dichloromethane to give an off-white solid (1.02 g, 86percent) LC/MS (LCT1): Rt 2.45 [M+H]+ 173, 171. |
86% | for 48 h; Heating / reflux | 6B. 6-Chloro-7,9-dihydropurin-8-oneA mixture of the 5,6-diamino-4-chloropyrimidine of Example 6A (1.0 g, 6.92 mmol) and N,N'-carbonyldiimidazole (2.13 g, 13.2 mmol) in 1,4-dioxane (20 ml) was refluxed under argon for 48 hours. The solution was concentrated to a brown oil, which was triturated and washed with dichloromethane to give an off-white solid (1.02 g, 86percent) LC/MS (LCTl): Rt2.45 [M+H]+ 173, 171. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | for 16 h; Heating / reflux | Synthesis 20-1 -A; 6-Chloro-7H-purin-8(9H)-one; NXrNH2 A mixture of 4-chloropyrimidine-2,3-diamine (36 mg, 0.25 mmol) and di(/V-succinimidyl)carbonate (128 mg, 0.50 mmol) in acetonitrile (10 mL) was refluxed for 16 hours. The solids formed were collected, washed with acetonitrile (2 x 5 mL) and dried, to give the title compound as a light yellow powder (33 mg, 78percent).1H NMR (500 MHz, de-DMSO) δ 8.35 (1 H, s), 11.90 (2H, s, broad); LC-MS (2) R1 1.96 min; m/z (ESI) 171 [MH+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | at 120℃; | Step 2: A solution of 6-chloropyrimidine-4,5 -diamine (432 mg, 3.0 mmol) in acetic anhydride (5 mL) was heated to 120 °C for overnight. The reaction mixture was concentrated and water was added, and then extracted with EtOAc. The organic layer was separated and washed with water and brine, dried over Na2S04 and concentrated. The residue was suspended in POCI3 (10 mL) and heated to 120 °C for overnight. The reaction was concentrated and diluted with EtOAc and sat. NaHC03 solution. The organic layer was separated and washed with water and brine, dried over Na2S04 and concentrated. Purified by a flash column chromatography (0-30percent EtOAc in petroleum ether) to give the desired product 6-chloro-8-methyl-9H-purine (263 mg, 52percent yield). LC-MS: m/z 169 (M+H)+. |
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