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CAS No. : | 100707-39-9 | MDL No. : | MFCD00466678 |
Formula : | C6H5BrN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MDERWSRHRJUWNS-UHFFFAOYSA-N |
M.W : | 217.02 | Pubchem ID : | 256210 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 41.66 |
TPSA : | 63.08 Ų |
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) : | -6.81 cm/s |
Log Po/w (iLOGP) : | 1.22 |
Log Po/w (XLOGP3) : | 1.15 |
Log Po/w (WLOGP) : | 1.25 |
Log Po/w (MLOGP) : | 0.32 |
Log Po/w (SILICOS-IT) : | 1.4 |
Consensus Log Po/w : | 1.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.25 |
Solubility : | 1.23 mg/ml ; 0.00565 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.07 |
Solubility : | 1.85 mg/ml ; 0.00853 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.27 |
Solubility : | 1.16 mg/ml ; 0.00533 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 |
---|---|---|
61% | for 2 h; Reflux | A mixture of compound 5-bromo-2-methylpyrimidine-4-carboxylic acid (350 mg,1.6 mmol) in xylene (5 mL) was refluxed for 2 h. After cooling, the mixture was applied directly to a silica column, which was eluted with petroleum ether, then ethyl acetate in petroleum ether (5percent v/v) to give compound 0601-120 (170 mg, 61 >) as a white solid. LCMS: 173 [M+l]+, 1H NMR (400 MHz, DMSO-d6): δ 2.59 (s, 3H), 8.87 (s, 2H). |
61% | for 2 h; Reflux | A mixture of compound 5-bromo-2-methylpyrimidine-4-carboxylic acid (350 mg, 1.6 mmol) in xylene (5 mL) was refluxed for 2 h. After cooling, the mixture was applied directly to a silica column, which was eluted with petroleum ether, then ethyl acetate in petroleum ether (5percent v/v) to give compound 0601-120 (170 mg, 61percent) as a white solid. LCMS: 173 [M+1]+, 1H NMR (400 MHz, DMSO-d6): δ 2.59 (s, 3H), 8.87 (s, 2H). |
61% | for 2 h; Reflux | A mixture of xylenes (5 mL) solution of compound 5-bromo-2-methyl-pyrimidine-4-carboxylic acid (350mg, 1.6mmol) was refluxed for 2 hours. After cooling, the mixture directly subjected to a silica column, petroleum ether, and then give the compound 0601-120 eluting with ethyl acetate in petroleum ether (5percent v / v) as a white solid (170mg, 61percent). |
27.3% | at 150℃; for 16 h; | A solution of KR-i 3 (i .46 g, 6.76 mmol) in xylene (20 mL) was heated iSO 00 for i6 h. After cooling to r.t., the mixture was purified by column to give thedesired product KR-i4 (0.3 g, 27.3percent) as a pale yellow solid. ESI-MS (M+i):i73calc.forC5H5BrN2: i72.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | Stage #1: With sodium ethanolate In ethanol at 50℃; Stage #2: With sodium ethanolate In ethanol |
Step 42a: 5-Bromo-2-methylpyrimidine (Compound 0601-120)Sodium (356 mg, 15.5 mmol) was carefully added to ethanol (5.9 mL) to prepare sodium ethoxide solution in ethanol. The above freshly prepared sodium ethoxide in ethanol solution (3.5 mL) was added to a stirred suspension of acetamidine hydrochloride (0.91 g, 9.69 mmol). The mixture was warmed to 50 °C, then the heating bath was removed and a solution of mucobromic acid (1 g, 3.87 mmol) in ethanol was added dropwise at a rate which maintained a constant temperature, followed by a further sodium ethoxide in ethanol solution (2 mL). After cooling, the mixture was filtered and evaporated to a residue which was shaken vigorously with hydrochloric acid (2 M x 2.4 mL). The brown precipitate was filtered and washed with cold water, then freeze-dried to give 5-bromo-2- methylpyrimidine-4-carboxylic acid (350 mg, 42percent) as a brown solid. LCMS: 218 [M+l]+, 1H NMR (400 MHz, DMSO-d6): δ 2.62 (s, 3H), 9.03 (s, 1H). |
42% | at 50℃; | Step 42a: 5-Bromo-2-methylpyrimidine (Compound 0601-120)[0365]Sodium (356 mg, 15.5 mmol) was carefully added to ethanol (5.9 mL) to prepare sodium ethoxide solution in ethanol. The above freshly prepared sodium ethoxide in ethanol solution (3.5 mL) was added to a stirred suspension of acetamidine hydrochloride (0.91 g, 9.69 mmol). The mixture was warmed to 50° C., then the heating bath was removed and a solution of mucobromic acid (1 g, 3.87 mmol) in ethanol was added dropwise at a rate which maintained a constant temperature, followed by a further sodium ethoxide in ethanol solution (2 mL). After cooling, the mixture was filtered and evaporated to a residue which was shaken vigorously with hydrochloric acid (2 M×2.4 mL). The brown precipitate was filtered and washed with cold water, then freeze-dried to give 5-bromo-2-methylpyrimidine-4-carboxylic acid (350 mg, 42percent) as a brown solid. LCMS: 218 [M+1]+, 1H NMR (400 MHz, DMSO-d6): δ2.62 (s, 3H), 9.03 (s, 1H). |
42% | With sodium ethanolate In ethanol at 50℃; | Sodium (356mg, 15.5mmol) was added to the carefully ethanol (5.9mL), and in ethanolSodium ethoxide solution was prepared. Sodium ethoxide in freshly prepared ethanol solution of the above (3.5 mL) was added to a stirred suspension of acetamidine hydrochloride (0.91g, 9.69mmol). The mixture was allowed to warm up to 50 , and then the heating bath was removed, Mukoburomu acid (1g, 3.87mmol) a solution in ethanol, was dropped so that a constant temperature is maintained, then further, ethanol solution (2mL) sodium ethoxide was dropped of. After cooling, the mixture was filtered, and the residue was evaporated, stirred vigorously with hydrochloric acid (2Mx2.4mL). The brown precipitate was filtered, washed with cold water, and then to obtain a freeze-dried to give 5-bromo-2-methyl-pyrimidine-4-carboxylic acid (350mg, 42percent) as a brown solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25.2% | With sodium ethanolate In ethanol at 20 - 50℃; for 17 h; | To a solution of the commercially available ethanimidamide ii, ashydrochloride, (6.0 g, 63.83 mmol) in anhydrous EtOH (20 mL) was added sodium ethoxide (20 mL of a 2i percent solution in ethanol) and the reactionmixture was stirred at 50 00 and the commercially available (2E)-2,3-dibromo-4-oxobut-2-enoic acid i 2 (6.82 g, 26.74 mmol) in EtOH (i 0 mL) was added into the mixture. After stirring at 50 00 for i hour, a further portion of sodiumethoxide (i 0 mL of a 2i percent solution in ethanol) was added and the mixture was stirred at r.t. for i6 h. The reaction mixture was filtrated and the filtratereduced in vacuo. The residue was then treated with 2 M aqueoushydrochloric acid (30 mL) and stirred vigorously for 30 mm. The resulting solid was filtrated, washed with water and air dried to give KR-i 3 (i .46 g, 25.2percent) as a pale yellow solid. ESI-MS (M+i): 2i7 calc. for C6H5BrN2O2:2i6.0. |
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