Methanol → Methyl 4-(2-(6-chloro-2-methylpyrimidin-4-ylamino)thiazol-5-ylthio)picolinate

Participants

Reaction Steps

A solution of N-(6-chloro-2-methylpyrimidin-4-yl)-5-thiocyanatothiazol-2-amine (˜0.725 g, ˜2.56 mmol, crude, described in Synthesis of thiocyanates, Example C, Table 2) and dithiothreitol (373 mg, 2.418 mmol) in MeOH (12 mL) was stirred for 2 hours, then DMF (20 mL), methyl 4-chloro-2-picolinamide (202 mg, 1.177 mmol) and K3PO4 (127 mg, 0.597 mmol) were added. The reaction was stirred for 1.5 hours, then poured into water (˜125 mL) and allowed to sit overnight for complete precipitation. The solid was collected by filtration, washed with water and vacuum dried to afford the title material (299 mg, 64% over 2 steps) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 12.39 (1H, s), 8.52 (1H, d, J=5.31 Hz), 7.91 (1H, s), 7.71 (1H, d, J=1.52 Hz), 7.37 (1H, dd, J=5.31, 2.02 Hz), 6.92 (1H, s), 3.82 (3H, s), 2.52 (3H, s). LC/MS (M+H)+: 394, 396. HPLC ret. time (Condition I): 1.652 min.

Provenance & Evidence