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CAS No. : | 95928-49-7 | MDL No. : | MFCD09991546 |
Formula : | C7H8N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CFWYVWBOCSWZIK-UHFFFAOYSA-N |
M.W : | 168.15 | Pubchem ID : | 10658232 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.29 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 40.94 |
TPSA : | 72.05 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) : | -7.52 cm/s |
Log Po/w (iLOGP) : | 1.22 |
Log Po/w (XLOGP3) : | -0.28 |
Log Po/w (WLOGP) : | -0.05 |
Log Po/w (MLOGP) : | -0.22 |
Log Po/w (SILICOS-IT) : | 1.18 |
Consensus Log Po/w : | 0.37 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.88 |
Solubility : | 22.3 mg/ml ; 0.132 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.77 |
Solubility : | 28.3 mg/ml ; 0.168 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.03 |
Solubility : | 1.55 mg/ml ; 0.00925 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.47 |
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 |
---|---|---|
52% | for 2 h; Reflux | Step d: Ethyl 2-chloropyrimidine-5-carboxylate (Compound R-2-1) A mixture of compound 204 (38.0 g, 153 mmol) and phosphoryl trichloride (300 mL) and N,N-dimethylaniline (3 mL) was heated at reflux for 2 h, cooled to room temperature and concentrated. The residue was quenched carefully with ice-water, adjusted pH to 7-8 with sodium carbonate and extracted with EtOAc. The combined organics were washed with ice-water and brine, dried over Na2SO4, evaporated, and purified by column chromatography (eluted with EtOAc/Hexanes, 10percent) to afford compound R-2-1 (15 g, 52percent) as a white solid. LCMS: 187 [M+1]+. 1H NMR (400 MHz, CDCl3): δ 1.36 (t, J=7.5 Hz, 3H), 4.39 (q, J=7.5 Hz, 2H), 9.08 (s, 2H). |
52% | With <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate In <i>N</i>,<i>N</i>-dimethyl-aniline for 2 h; Reflux | A mixture of compound 204 (38.0 g, 153 mmol) and phosphoryl trichloride (300 mL) and N, N-dimethylaniline (3 mL) was heated at reflux for 2 h, cooled to room temperature and concentrated. The residue was quenched carefully with ice-water, adjusted pH to 7-8 with sodium carbonate and extracted with EtOAc. The combined organics were washed with ice-water and brine, dried over Na2SO4, evaporated, and purified by column chromatography (eluted with EtOAc/Hexanes, 10percent) to afford compound R-2-1 (15 g, 52percent) as a white solid. LCMS: 187 [M+ljt ‘H NMR (400 MHz, CDC13): ö 1.36 (t, J 7.5 Hz, 3H), 4.39 (q, J 7.5 Hz, 2H), 9.08 (s, 2H). |
30% | Stage #1: With trichlorophosphate In <i>N</i>,<i>N</i>-dimethyl-aniline for 1.5 h; Heating / reflux Stage #2: at 0℃; |
Step 11d: Ethyl 2-chloropyrimidine-5-carboxylate (Compound 0405) A mixture of 0404 (3.60 g, 21 mmol), phosphorus oxychloride (25 mL), and N,N-dimethylaniline (2.5 mL) was heated to reflux for 1.5 h. After removal of the solvent, ice water (10 mL) was added to the residue. The mixture was added to 2 N NaOH (90 ml), and extracted with EtOAc. After work up the residue was purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 5percent v/v) to give product 0405 (1.20 g, 30percent): LCMS: 187 [M+1]+, 1H NMR (300 MHz, CDCl3): δ 1.42 (t, J=7.5 Hz, 3H), 4.48 (q, J=7.5 Hz, 2H), 9.15 (s, 2H); 1H NMR (400 MHz, DMSO-d6): δ 1.33 (t, J=6.8 Hz, 3H); 4.37 (q, J=6.8 Hz, 2H), 9.18 (s, 2H). |
30% | Stage #1: for 1.5 h; Reflux Stage #2: With sodium hydroxide In waterCooling with ice |
Step lOd: Ethyl 2-chloropyrimidine-5-carboxylate (Compound 0305)A mixture of compound 0304 (3.60 g, 21 mmol), phosphorus oxychloride ( 25 mL), and N,N-dimethylaniline (2.5 mL) was heated at reflux for 1.5 h. After removal of the solvent, ice water (10 mL) was added to the residue. The mixture was added to 2 N NaOH (90 ml), and extracted with EtOAc. The organic layer was evaporated and purified by column chromatography (ethyl acetate in petroleum ether, 5percent v/v) to give compound 0305 (1.20 g, 30percent): LCMS: 187 [M+l]+, 1H NMR (300 MHz, CDC13): δ 1.42 (t, J= 7.5 Hz , 3H), 4.48 (q, J= 7.5 Hz, 2H), 9.15 (s, 2H); 1H NMR (400 MHz, DMSO-d6): δ 1.33 (t, J = 6.8 Hz, 3H); 4.37 (q, J= 6.8 Hz, 2H), 9.18 (s, 2H). |
30% | for 1.5 h; Reflux | Step 17d: Ethyl 2-chloropyrimidine-5-carboxylate (Compound 0605)A mixture of 0604 (3.60 g, 21 mmol), phosphorus oxychloride (25 mL), and N,N-dimethylaniline (2.5 mL) was heated to reflux for 1.5 h. After removal of the solvent, ice water (10 mL) was added to the residue. The mixture was added to 2 N NaOH (90 ml), and extracted with EtOAc. After work up the residue was purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 5percent v/v) to give product 0605 (1.20 g, 30percent): LCMS: 187 [M+l]+, 1H NMR (300 MHz, CDC13): δ 1.42 (t, J= 7.5 Hz , 3H), 4.48 (q, J= 7.5 Hz, 2H), 9.15 (s, 2H); 1H NMR (400 MHz, DMSO-d6): δ 1.33 (t, J= 6.8 Hz, 3H); 4.37 (q, J= 6.8 Hz, 2H), 9.18 (s, 2H). |
30% | With trichlorophosphate In <i>N</i>,<i>N</i>-dimethyl-aniline; Petroleum ether for 1.5 h; Reflux | Step 10d: Ethyl 2-chloropyrimidine-5-carboxylate (Compound 0305)[0216]A mixture of compound 0304 (3.60 g, 21 mmol), phosphorus oxychloride (25 mL), and N,N-dimethylaniline (2.5 mL) was heated at reflux for 1.5 h. After removal of the solvent, ice water (10 mL) was added to the residue. The mixture was added to 2 N NaOH (90 ml), and extracted with EtOAc. The organic layer was evaporated and purified by column chromatography (ethyl acetate in petroleum ether, 5percent v/v) to give compound 0305 (1.20 g, 30percent): LCMS: 187 [M+1]+, 1H NMR (300 MHz, CDCl3): δ 1.42 (t, J=7.5 Hz, 3H), 4.48 (q, J=7.5 Hz, 2H), 9.15 (s, 2H); 1H NMR (400 MHz, DMSO-d6): δ 1.33 (t, J=6.8 Hz, 3H); 4.37 (q, J=6.8 Hz, 2H), 9.18 (s, 2H). |
1.2 g | With trichlorophosphate In N,N-dimethyl-formamide for 1.5 h; Reflux | Compound 0304 (3.60g, 21mmol), phosphorous oxychloride (25 mL), and N, was heated for 1.5 hours under reflux N- mixture of dimethyl aniline (2.5 mL). After removal of the solvent, it was added ice-water (10 mL) to the residue. The mixture was added to 2N NaOH (90ml), and extracted with EtOAc. The organic layer was evaporated and purified by column chromatography (petroleum ether containing ethyl acetate, 5percent v / v), compound 0305 (1.20g, 30percent) was obtained: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | for 8 h; Reflux | Compound15 (168 mg, 1.0 mmol) was dissolved in POCl3, and thenrefluxed for 8 h. The extra POCl3 was removed by depressed pressuredistillation. The residues were treated with ice, and the precipitatewas filtered and washed by water to give compound 16(180 mg, 56percent) as a yellow solid. 1H NMR (300 MHz, CDCl3) d:9.16 (s, 2H), 4.46 (q, J = 6.0 Hz, 2H), 1.43 (t, J = 6.0 Hz, 3H). |
45% | Stage #1: for 1.5 h; Reflux Stage #2: With sodium hydroxide In water; ethyl acetate |
A mixture of the compound 1 (2g, 12mmol), DMAP (1.32g, l lmmol) and POCl3 (20mL) was heated at reflux for 1.5h. After removal of the solvent, EA was added to the residual. The pH of the mixture was adjusted to 7 with aq. NaOH (2M), the organic layer was then separated, washed with brine. After removal of the solvent, the residual was extracted with PE and dried over Na2S04, evaporation of the solvent gave a light yellow solid (lg, 45percent). |
45% | Stage #1: for 1.5 h; Reflux Stage #2: With sodium hydroxide In water |
Synthesis of intermediate 2A mixture of the compound 1 (2g , 12 mmol), N,N'-dimethylaminopyridine (DMAP) (1.32 g, 11 mmol) and POCl3 (20 mL) was heated at reflux for 1.5h. After removal of the solvent, EA was added to the residual. The pH of the mixture was adjusted to 7 with aq. NaOH (2M), the organic layer was then separated, washed with brine. After removal of the solvent, the residual was extracted with PE and dried over Na2S04, evaporation of the solvent gave a light yellow solid (1 g, 45percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | for 1.5 h; Heating / reflux | Step 11c: Ethyl 2-oxo-1,2-dihydropyrimidine-5-carboxylate (Compound 0404) A solution of 0403 (2.50 g, 14.7 mmol) and bromine (2.40 g, 15 mmol) in acetic acid (55 mL) was heated to reflux for 1.5 h. Removal of the solvent afforded crude product 0404 (3.60 g, 99percent): LCMS: 169 [M+1]+, 1H NMR (400 MHz, CDCl3): δ 1.27 (t, J=7.2 Hz, 3H), 4.28 (q, J=7.2 Hz, 2H), 8.85 (s, 2H), 12.19 (ds, 2H). |
54% | for 2 h; Reflux | To a solution of compound 203 (47 g, 280 mmol) in acetic acid (500 mL) was added bromine (49.0 g, 307 mmol). The mixture was heated at reflux for 2 h, cooled to room temperature, further cooled at 0-5°C and filtered to give the title compound 204 as a yellow solid (38 g, 54percent). LCMS: 169 [M+ljt ‘H NMR (400 MHz, D20): ö 1.28 (t, J 7.2 Hz, 3H), 4.32 (q, J 7.2 Hz, 2H), 9.00 (br, s, 2H). |
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