Aminoacetonitrile → ethyl 4-(3-(3-(cyanomethyl)ureido)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Participants

Reaction Steps

To a mixture of ethyl 4-(3-aminophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (103 mg, 0.250 mmol), DIPEA (0.131 mL, 0.749 mmol) in DCM (1 mL) was added CDI (81 mg, 0.50 mmol). The reaction mixture was stirred at room temperature overnight. At that point aminoacetonitrile (70.0 mg, 1.25 mmol) was added and the reaction mixture was stirred at room temperature for 5 hours. The resulting mixture was concentrated and purified by chromatography on silica eluting with 0-100% ethyl acetate/hexanes to give ethyl 4-(3-(3-(cyanomethyl)ureido)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate as a pale yellow solid. LRMS (ESI) calc'd for C24H31N6O4Si [M+H]+: 495, found 495.

Provenance & Evidence