Hydrochloric Acid → 1-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-4-morpholinothieno[3,2-d]pyrimidine 4, Example 2) (1.0 eq) dissolved in THF (0.1M) at −78° C. was added a solution of n-butyllithium (1.3 eq, 1.6M in hexanes) following General Procedure D. The reaction mixture was stirred at −40° C. for 30 minutes. N,N-dimethylacetamide (4.0 eq) was added and reaction mixture was allowed to slowly warm up to 0° C. and stirred for 2 hours. Reaction mixture was poured in a cold solution of 0.25M HCl, and extracted with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated. The crude reaction mixture was purified by flash chromatography to yield 1-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)ethanone.

Provenance & Evidence