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

Participants

Reaction Steps

To a solution of 4,6-dichloro-2-methylpyrimidine (Aldrich) (2.000 g, 12.27 mmol) in THF (25 mL) was added sodium thiomethoxide (Aldrich) (0.903 g, 12.88 mmol). The reaction mixture was stirred at rt under N2 for 3 h. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×15 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (120 g, 5% to 10% acetone in hexanes) to afford the product as white solid (1.3 g). MS (ESI pos. ion) m/z: 174.9. 1H NMR (300 MHz, CDCl3) δ ppm 2.57 (s, 3H) 2.65 (s, 3H) 7.02 (s, 1H).

Provenance & Evidence