2-Pyrimidinecarboxylicacid,5-methyl-,methylester(6CI,9CI)

To a solution of 2-chloro-5-methyl-pyrimidine (500.00 mg, 3.89 mmol, 1.00 eq) in MeOH (10.00 mL) and DMF (2.00mL) was added triethylamine (1.18 g, 11.67 mmol, 1.62 mL, 3.00 eq) and Pd(dppf)C12 (426.87 mg, 583.39 umol, 0.15 eq) under CO. The suspension was degassed and purged with CO several times. The mixture was stirred under CO (3 Mpa) at 120°C for 16 h. The reaction mixture was filtered and the filtrate was concentrated. The crude residue was purified by column chromatography (Petroleum ether : Ethyl acetate=20: l to 0: 1) to afford methyl 5-methylpyrimidine-2-carboxylate (350.00 mg). LCMS (M+HTo a solution of methanol (50 mL) was added SOClTo a solution of methyl 5-methylpyrimidine-2-carboxylate [Example 9, Step 2] (2 g, 13.2 mmol, 1.00 equiv) in MeOD (30 mL) was added NaBD4 (1.66 g, 39.2 mmol, 3.00 equiv) at 0 C. The resulting solution was stirred for 3 h at 25 C. The reaction was then quenched by the addition of D2O (10 mL). The resulting mixture was concentrated under vacuum to remove MeOD. The resulting solution was extracted with ethyl acetate (3×20 mL). The organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford 1.5 g (90.2%) of (5-methylpyrimidin-2-yl)(d2)methanol as a yellow solid. LC-MS: m/z=127[M+H]+.To a solution of methanol (50 mL) was added SOCl2 (5.17 g, 43.5 mmol, 3.00 equiv) dropwise at 0 C. The resulting solution was stirred for 0.5 h at 25 C. This was followed by the addition of 5-methylpyrimidine-2-carboxylic acid [Example 9, Step 1] (2 g, 14.5 mmol, 1.00 equiv). The resulting solution was stirred for 1 h at 65 C. The resulting mixture was concentrated under vacuum to remove methanol and SOCl2. The resulting solution was diluted with H2O (30 mL). The resulting solution was extracted with ethyl acetate (3×30 mL). The organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford 2 g (90.7%) of methyl 5-methylpyrimidine-2-carboxylate as a yellow solid. LC-MS: m/z=153 [M+H]+.

Molecular Weight:152.15
XLogP3:-0.3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:152.058577502
Monoisotopic Mass:152.058577502
Topological Polar Surface Area:52.1
Heavy Atom Count:11
Complexity:141
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes