Dimethylformamide → 4-(Methylthio)furo[3,2-d]pyrimidine-6-carbaldehyde

Participants

Reaction Steps

Butyl lithium (as 1.6 M in hexanes, 7 mL) was added to a solution of 4-(methylthio)furo[3,2-d]pyrimidine (Intermediate 85) (1.21 g) in THF (25 mL) at −70° C. The reaction was stirred for 5 minutes, DMF (5 mL) added, and the reaction mixture allowed to warm to ambient temperature. 30% Saturated ammonium chloride solution (50 mL) was added and the mixture extracted into EtOAc (3×50 mL). The combined organics were washed with 50% saturated sodium carbonate solution (50 mL), water (50 mL), dried and the solvent removed to afford the title compound as a pale yellow solid (1.02 g) (the product contained 20% unreacted starting material but was used without further purification in subsequents steps);

Provenance & Evidence