Triethylamine → ethyl 4-(3-(2-(methylsulfonamidomethyl)acrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-(3-(2-(aminomethyl)acrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (32 mg, 0.088 mmol) in DCM (438 μL) was added triethylamine (12 μL, 0.088 mmol) and methanesulfonyl chloride (7.5 μL, 0.096 mmol) at 0° C. The reaction mixture was allowed to stir at 0° C. for 1 hour and then gradually warmed up to room temperature over 1 hour. The resulting mixture was diluted with DCM (2 mL) and washed with saturated aqueous sodium bicarbonate solution (2 mL). The aqueous layer was extracted with DCM (×3) and the combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier to give ethyl 4-(3-(2-(methylsulfonamidomethyl)acrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C20H22N5O5S [M+H]+: 444, found 444. 1H NMR (600 MHz, DMSO-D6) δ 12.99 (bs, 1H), 10.11 (s, 1H), 8.90 (s, 1H), 8.30 (s, 1H), 8.05 (s, 1H), 7.84 (d, J=8.21 Hz, 1H), 7.42 (t, J=8.21 Hz, 1H), 7.38 (t, J=6.45 Hz, 1H), 7.33 (d, J=7.63 Hz, 1H), 6.01 (s, 1H), 5.75 (s, 1H), 3.89 (d, J=6.45 Hz, 2H), 3.86 (q, J=7.04 Hz, 2H), 2.94 (s, 3H), 0.86 (t, J=7.04 Hz, 3H).

Provenance & Evidence