4,6-Dichloro-2-methylpyrimidine → 4-Chloro-2-methyl-6-(methylthio)pyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4,6-dichloro-2-methylpyrimidine (11.5 g, 70.6 mmol, Aldrich) and sodium methanethiolate (5.93 g, 85 mmol, Aldrich) in toluene (50 mL) was stirred at 25° C. for 24 h. The reaction mixture was concentrated in vacuo. The residue was diluted with EtOAc, washed with brine, and dried over Na2SO4. The crude product was purified by recrystallization from hexane to give 4-chloro-2-methyl-6-(methylthio)pyrimidine (5.5 g, 31.5 mmol, 44.6% yield) as white crystals. 1H NMR (400 MHz, CDCl3) δ 7.01 (s, 1H); 2.64 (s, 3H); 2.56 (s, 3H). m/z (ESI, +ve ion) 175 (M+H)+.

Provenance & Evidence