METHYL 5-BROMO-4-PYRIMIDINECARBOXYLATE

5-Bromo-4-pyrimidine carboxylic acid 1-84 (858 mg, 4.23 mmol) was dissolved in MeOH (15 mL) and thionyl chloride (77 μ, 1 .06 mmol) added dropwise at rt. The reaction mixture was heated to 70°C and stirred at this temperature for 3 h. The reaction mixture was then cooled to rt and evaporated to dryness. The residue was re-dissolved in a mixture of water (25 mL) and saturated aq. NaHCOs (25 mL) before extracting with EtOAc (3 x 50 mL). The combined organic extracts were then washed with saturated aqueous NaHCOs (40 mL) and brine (40 mL) before drying over MgS04. Concentration in vacuo provided the title compound as a brown solid (502 mg, 2.31 mmol, 55percent).Process 4 5-Bromopyrimidine-4-carboxylic acid (prepared according to the procedure described in U.S. Pat. No. 4, 110, 450) (1.0 eq, 6.14 g, 30.2 mmol) was suspended in CH5-bromopyrimidine-4-carboxylic acid (prepared according to the procedure described in U.S. Pat. No. 4, 110, 450) (1.0 eq, 6.14 g, 30.2 mmol) was suspended in CHA mixture of (0.47 g, 2.16 mmol), 2, 5-dichlorophenol (0.39 g, 2.39 mmol) Potassium carbonate (0.6 g, 4.34 mmol), Cuprous iodide (41 mg, 0.22 mmol) and copper powder (41 mg, 0.64 mmol) were dissolved in N, N-dimethylformamide (3 mL) Microwave heated to 120 C for 0.5 hours. The reaction solution was cooled to room temperature, filter, The filtrate was poured into water (20 mL) Ethyl acetate (20 mL x 3) was added, Combine organic phase, Washed with saturated aqueous sodium chloride solution (10 mL) Dried over anhydrous sodium sulfate, filter, concentrate, The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10: 1) to give the title compound (0.12 g, yield 18.5%). (13g, 60mmol), phenylboronic acid (7.3g, 60mmol), 2M Na2CO3 (aq) (120ml, 240mmol) and Pd(PPh3)4 (1.8g, 1.2mmol) in an N2 atmosphere was dissolved in 400ml of toluene / 130ml of ethanol. After stirring at 80 deg. C for 24 hours the mixture was cooled to room temperature. With dichloromethane / aqueous the residue was extracted, and the organic layer was evaporated to dryness. The residue was purified by column chromatography on silica gel to give 5.9g 5-phenylpyrimidine-4-carboxylic acid methyl ester. Yield 45.4%.

Molecular Weight:217.02
XLogP3:1.1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:215.95344
Monoisotopic Mass:215.95344
Topological Polar Surface Area:52.1
Heavy Atom Count:11
Complexity:154
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes