Dimethylformamide → 2-Chloro-4-morpholinothieno[2,3-d]pyrimidine-6-carbaldehyde

Participants

Reaction Steps

Also, to a suspension of 4-(2-chlorothieno[2,3-d]pyrimidin-4-yl)morpholine (1.75 g, 6.85 mmol) in dry THF at −78° C. was added a 2.5M solution of n-butyllithium (nBuLi) in hexane (3.3 mL, 1.2 eq.). After stirring for 1 h, dry DMF (796 uL, 1.5 eq.) was added. The reaction mixture was stirred for 1 h at −78° C. and then warmed slowly to room temperature. After a further 2 h at room temperature the reaction mixture was poured onto ice/water yielding a yellow precipitate. This was collected by filtration and air-dried to yield 2-chloro-4-morpholinothieno[2,3-d]pyrimidine-6-carbaldehyde (1.5 g, 77% yield) MS (Q1) 284 (M)+

Provenance & Evidence