Diisopropylamine → Ethyl 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, to a solution of diisopropylamine (15.7 mL, 112 mmol) in THF (70 mL) was added dropwise butyllithium (1.6M hexane solution, 70 mL, 112 mmol) at −78° C. The mixture was stirred at 0° C. for 30 min and cooled to −78° C. A solution of 4,6-dichloro-2-(methylsulfanyl)pyrimidine (14.12 g, 72.4 mmol) in THF (20 mL) was added dropwise thereto, and the mixture was stirred at −78° C. for 1 hr. A solution of ethyl chlorocarbonate (13.9 mL, 145 mmol) in THF (20 ml) was added dropwise thereto, and the mixture was stirred at −78° C. for 30 min, and then at 0° C. for 30 min. Water was added thereto, and the mixture was extracted twice with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluate, hexane:ethyl acetate=100:0→90:10) to give the title compound (13.28 g, 69%) as a colorless solid.

Provenance & Evidence