Diisopropylamine → 1-(3-Bromophenyl)-2-(2-methylthiopyrimidin-4-yl)-ethanone

Participants

Reaction Conditions

Reaction Steps

19.8 ml (140 mmol) diisopropylamine were dissolved in 250 ml dry tetrahydrofurane and cooled to −75° C. and 87.6 ml of a solution of n-butyllithium (1.6 M in hexane, 140 mmol) was added over a period of 20 minutes. After stirring for 15 minutes at −75° C. a solution of 13.1 g (93 mmol) 2-methylthio-4-methylpyrimidine in 80 ml dry tetrahydrofurane was added within 30 minutes at −75° C. and the mixture was stirred for additional 15 minutes. Then a solution of 25.1 g (103 mmol) B1 was added within 30 minutes at −75° C. The mixture was allowed to warm up to room temperature and was poured on 600 ml ethyl acetate/water (1:1). The aqueous layer was extracted with 50 ml ethyl acetate and the combined organic layers were dried over sodium sulphate. Removal of the solvent in vacuo yielded 23.3 g (77%) C1, m.p. 98-101° C.

Provenance & Evidence