Methyl iodide → 4,6-Dimethyl-2-(methylsulfanyl)pyrimidine

Participants

Reaction Steps

A suspension of potassium carbonate (27.6 g, 0.2 mol) in a solution of 4,6-dimethyl-2-mercaptopyrimidine (14 g, 0.1 mol) and methyl iodide (18.7 ml, 0.3 mol) in acetone (200 ml) was heated under reflux for 3 hours. The reaction mixture was allowed to cool before being filtered and then evaporated in vacuo. Distillation of the mixture at a pressure of 0.01 mmHg afforded 12.7 g 2-methylthio-4,6-dimethylpyrimidine as a white solid. A portion of this solid (4.42 g, 28.7 mmol) was dissolved in dichloromethane (200ml) and m-chloroperoxybenzoic acid (50%, 22.8 g, 66.0 mmol) was added in portions. The resulting mixture was stirred for a period of 5 days at the end of which it was first filtered and then evaporated in vacuo. Purification by flash column chromatography upon silica gel using diethyl ether as eluant afforded 3.35 g 2-methylsulphonyl-4,6-dimethylpyrimidine as a white solid, m.pt., 81° C.

Provenance & Evidence