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CAS No. : | 89581-38-4 | MDL No. : | MFCD11111606 |
Formula : | C6H5BrN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XILAKTMDKMVJQV-UHFFFAOYSA-N |
M.W : | 217.02 | Pubchem ID : | 45790831 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.01 |
TPSA : | 52.08 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) : | -7.64 cm/s |
Log Po/w (iLOGP) : | 1.84 |
Log Po/w (XLOGP3) : | -0.02 |
Log Po/w (WLOGP) : | 1.03 |
Log Po/w (MLOGP) : | 0.32 |
Log Po/w (SILICOS-IT) : | 1.41 |
Consensus Log Po/w : | 0.91 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.44 |
Solubility : | 7.8 mg/ml ; 0.0359 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.62 |
Solubility : | 51.6 mg/ml ; 0.238 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.59 |
Solubility : | 0.56 mg/ml ; 0.00258 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.74 |
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 |
---|---|---|
67% | for 0.25 h; Reflux | To a solution of 5-bromopyrimidine-2-carboxylic acid (3.22 g, 15.9 mmol) in MeOH (50 mL) at room temperature was added acetyl chloride (4.0 mL, 56.3 mmol). The reaction mixture was heated to reflux for 15 min, cooled to room temperature and concentrated under reduced pressure. The reaction mixture was diluted with saturated NaHCC>3 (30 mL) and EtOAc, and transferred to a separatory funnel. The aqueous phase was extracted with EtOAc (4 x) and the combined organic extracts were washed with brine (1 x), dried over MgS04, filtered, and concentrated to give methyl 5- bromopyrimidine-2-carboxylate (2.30 g, 10.6 mmol, 67 percent yield) as a white solid. LC/MS (ESI) m/z = 216.9 (M+H). Calculated for 0ΒΓΝ202 216.0 |
67% | for 0.25 h; Reflux | To a solution of 5-bromopyrimidine-2-carboxylic acid (3.22 g, 15.9 mmol) in MeOH (50 mL) at room temperature was added acetyl chloride (4.0 mL, 56.3 mmol). The reaction mixture was heated to reflux for 15 min, cooled to room temperature and concentrated under reduced pressure. The reaction mixture was diluted with saturated NaHCO3 (30 mL) and EtOAc, and transferred to a separatory funnel. The aqueous phase was extracted with EtOAc (4 x) and the combined organic extracts were washed with brine (1 x), dried over MgSO4, filtered, and concentrated to give methyl 5- bromopyrimidine-2-carboxylate (2.30 g, 10.6 mmol, 67percent yield) as a white solid. LC/MS (ESI+) m/z = 216.9 (M+H). Calculated for C6H5BrN2O2216.0 |
57% | at 0 - 20℃; for 18 h; | Preparation 65 5-Bromo-pyrimidine-2-carboxylic acid methyl ester Fuming hydrochloric acid was passed through an ice-cooled SOTUTIBN OF THE- product of preparation 64 (5. 5g. 27mmol) in methanol (50mL) until saturated The reaction mixture was warmed to room temperature and was stirred for 18- hours. The solvent was then evaporated under reduced pressure and. the- residue was dissolved in dichloromethane, washed with water and sodium HYDROGEN CARBONATE SOLUTION, DRIED-OVER MAGNESIUM SULFATE. AND CONCENTRATED IN-: O AFFORD THE"TITLE compound as yellow. solid in 57percent yield, 3.5g. HNMR (CDC) 3. 400MHZ) .sect. : 4, 65 (s, 3H), 9. 00 (s, 2H). MS AP + |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With hydrogenchloride In water at 80℃; for 2 h; Inert atmosphere | To a solution of 5-bromopyrimidine-2-carbonitrile (3.0 g, 16 mmol) in MeOH (20 mL) was added concentrated HCl (19 mL). The reaction mixture was heated at 80° C. for 2 h. Upon cooling to rt, a precipitate formed. Filtration provided the desired product as a white solid (2.5 g, 71percent). MS (ESI): mass calcd. for C6H5BrN2O2, 216.0; m/z found, 217.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 9.20 (s, 2H), 3.92 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
294 mg | at 0℃; for 2 h; | To a solution of 5-bromopyrimidine-2-carboxylic acid (500 mg, 2.47 mmol) in DCM (5.0 mL), in a two-necked flask equipped with a bubbler, was added oxalyl chloride (0.23 mL, 2.72 mmol) and two drops of DMF at room temperature. After stirring for 1.5 h, the solvent was removed in vacuo. The acyl chloride was dissolved in CH2C12 (5.0 mL) and added MeOH (0.20 mL, 4.93 mmol) at 0 °C. After stirring for 2 h, the reaction mixture was quenched by adding saturated NaHCC solution. The crude products were extracted with CH2C12 (x3), and the combined organic extracts were washed with brine, dried (MgS04), and concentrated in vacuo. The residue was purified by flash column chromatography (hexane/EtOAc = 3/1 to 2/1) to afford desired methyl 5-bromopyrimidine-2-carboxylate (294 mg, 90percent) as a white solid. NMR (300 MHz, CDCh) δ 9.01 (s, 2H), 4.10 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With sodium tetrahydroborate In tetrahydrofuran; water at 0 - 20℃; | An solution of NaBH4 (510 mg, 2.70 mmol) in H2O (10 mL) was introduced drop-wise to a solution of methyl 5-bromopyrimidine-2-carboxylate (3.05 g, 14.1 mmol) in THF (100 mL) at 0° C. The mixture was allowed to warm slowly to RT overnight. The majority of the THF was evaporated, and the resulting residue was diluted with EtOAc (200 mL). The organic fraction was washed with brine (200 mL), dried (MgSO4) and purified over silica, eluting with 0-60percent EtOAc:n-heptane) to afford i (510 mg, 19percent). MS: 189.0 & 191.0; 1:1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With hydrazine hydrate In ethanol at 20℃; for 1 h; Inert atmosphere | To a slurry of methyl 5-bromopyrimidine-2-carboxylate (1.0 g, 4.6 mmol) in EtOH (3.6 mL) was added hydrazine monohydrate (0.46 mL, 9.2 mmol). The reaction mixture was stirred at rt for 1 h. The mixture was filtered, and the collected solid was washed with additional EtOH to provide the desired product as a beige solid (720 mg, 72percent). MS (ESI): mass calcd. for C5H5N4O, 216.0; m/z found, 217.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 10.15 (s, 1H), 9.18-9.08 (s, 2H), 4.67 (s, 2H). |
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