Triethylamine → 6-(2-Methoxyphenyl)-2-(methylthio)pyrimidine-4-carboxamide

Participants

Reaction Steps

To a stirred suspension of 6-(2-methoxyphenyl)-2-(methylthio)pyrimidine-4-carboxylic acid (9.8 g, 40 mmol), triethylamine (33 mL, 240 mmol), and ammonium chloride (11 g, 200 mmol) in DMF (40 mL) was added PyBOP (21.9 g, 42 mmol) in five portions. The reaction was complete in 2 h, as determined by LCMS analysis. The reaction mixture was poured into water (1.5 L) and stirred for 10 minutes. The precipitate was collected by filtration and dried overnight under high vacuum to give 6-(2-methoxyphenyl)-2-(methylthio)pyrimidine-4-carboxamide. 1H NMR (300 MHz, CDCl3) δ 8.40 (s, 0.7H), 8.05 (m, 1.3H), 7.74 (bs, 1H), 7.44 (m, 1H), 7.05 (m, 2H), 5.78 (bs, 1H), 3.92 (s, 3H); 2.65 (s, 3H). HPLC ret. time 2.71 min, 10-100% CH3CN, 5 min gradient; ESI-MS m/z 245.9 (M+H)+.

Provenance & Evidence