Sodium Carbonate → ethyl 4-(3-(N-methylacrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

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Reaction Steps

To a solution of ethyl 4-(3-(methylamino)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (96 mg, 0.32 mmol) in THF (3.0 mL) at room temperature was added acryloyl chloride (40 μL, 0.49 mmol), and the solution was allowed to stir at room temperature for 30 minutes. Saturated aqueous sodium carbonate (5 mL) was added and the mixture was extracted with ethyl acetate (×3). The combined organic layers were washed with water (10 mL), 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-(N-methylacrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C19H19N4O3 [M+H]+: 351, found 351. 1H NMR (600 MHz, DMSO-D6) δ 13.03 (bs, 1H), 8.92 (s, 1H), 8.33 (s, 1H), 7.61 (d, J=7.63 Hz, 1H), 7.55 (t, J=8.21 Hz, 1H), 7.47 (s, 1H), 7.75 (d, J=7.63 Hz, 1H), 7.39 (d, J=8.8 Hz, 1H), 6.17 (s, 1H), 5.57 (t, J=7.04 Hz, 1H), 3.94 (q, J=7.04 Hz, 2H), 3.27 (s, 3H), 0.96 (t, J=7.04 Hz, 3H).

Provenance & Evidence