Tributyltin Chloride → 2-Methyl-4-(methylthio)-6-(tributylstannyl)pyrimidine

Participants

Reaction Conditions

Reaction Steps

A solution of 4-iodo-2-methyl-6-(methylthio)pyrimidine (2.35 g, 8.83 mmol) in THF (20 mL) was cooled to −78° C. and treated dropwise with isopropylmagnesium chloride (2 N solution in THF, 2 mL, 4.0 mmol, Aldrich). After 10 min, chlorotributylstannane (2.4 mL, 8.83 mmol, Aldrich) was added. The mixture was stirred at −78° C. for 1 h, then warmed to room temperature and stirred overnight. The mixture was concentrated in vacuo and purified by flash column chromatography with alumina, eluting with a gradient of 0-10% EtOAc in hexane, to give 2-methyl-4-(methylthio)-6-(tributylstannyl)pyrimidine (2.5 g, 5.82 mmol, 65.9% yield) as colorless oil. This was used as such without further purification. m/z (ESI, +ve ion) 430 (M+H)+.

Provenance & Evidence