Water → 7-(Diisopropylamino)-2-(1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidine-5-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(1-methyl-4-phenyl-1H-imidazol-5-yl)-7-(methylthio)[1,3]thiazolo[5,4-d]pyrimidine (Intermediate 42) (0.1 g) in THF (4 mL) was added to a solution of LDA (2.2 eq) in THF (6 mL) at −78° C., under an inert atmosphere. The reaction mixture was stirred at −78° C. for 1 hours then DMF (0.4 mL) was added. The reaction mixture was stirred at −78° C. for a further 1 hours then poured into water (10 mL) and extracted with EtOAc (3×10 mL), washed with brine (10 mL), dried and the solvent evaporated in vacuo to give a brown oil. Purification by flash chromatography on silica, eluting with EtOAc:hexane (1:9) gave the title compound as a yellow oil (14 mg, 11%);

Provenance & Evidence