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

Participants

Reaction Conditions

Reaction Steps

Ethyl 4-(3-(3-(cyanomethyl)ureido)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (65.4 mg, 0.132 mmol) was mixed with 1 M TBAF in THF (2.64 mL, 2.64 mmol) and heated at 45° C. for 1 hour. The reaction mixture was diluted with ethyl acetate (5 mL) and washed with water (5 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica eluting with 0-20% MeOH/DCM to give ethyl 4-(3-(3-(cyanomethyl)ureido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (EST) calc'd for C18H17N6O3 [M+H]+: 365, found 365. 1H NMR (600 MHz, DMSO-D6) δ 12.96 (bs, 1H), 9.08 (s, 1H), 8.89 (s, 1H), 8.29 (s, 1H), 7.76 (s, 1H), 7.54 (d, J=8.21 Hz, 1H), 7.35 (t, J=7.63 Hz, 1H), 7.20 (d, J=7.63 Hz, 1H), 6.71 (d, J=5.28 Hz, 1H), 4.13 (d, J=5.87 Hz, 2H), 3.86 (q, J=6.8 Hz, 2H), 0.84 (t, J=7.04 Hz, 3H).

Provenance & Evidence