Water → 6-(1-Methyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)thieno[3,2-d]pyrimidine

Participants

Reaction Steps

Methylamine (2M in THF, 2.5 mL) was added to a solution of 4- (methylthio)thieno[3,2-d]pyrimidine-6-carbaldehyde (intermediate 21) (105 mg) in DCM (10 mL) containing 4 Å molecular sieves (1 g). The reaction mixture was stirred for 2.5 hours, at which point PhTosMIC (149 mg) and piperazine (90 mg) were added. The reaction was stirred for a further 72 hours then additional PhTosMIC (30 mg) was added. After stirring for a further 1.5 hours the mixture was poured into water and extracted into DCM, washed with water and brine, dried, and the solvent removed. Purification by flash chromatography on silica eluting with EtOAc:hexane (25:75 to 0:1Q0) gave the title compound as a pale solid foam (95 mg, 56%);

Provenance & Evidence