Chloride → HCID 89629990, compound

Participants

Reaction Steps

To a solution of methyl 4-(3-amino-4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (100 mg, 0.349 mmol) and DIPEA (183 μL, 1.05 mmol) in THF (1.7 mL) at room temperature was added methacyloyl chloride (36.5 mg, 0.349 mmol) and the solution was stirred for 1 hour. The desired product was purified by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier. The combined fractions with the desired product were concentrated until only the water layer remained. The water layer was neutralized with 2 M aqueous potassium carbonate and the mixture was extracted with ethyl acetate (×5). The combined organic fractions were dried with sodium sulfate, filtered and concentrated under reduced pressure to give methyl 4-{4-fluoro-3-[(2-methylacryloyl)amino]phenyl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C18H16FN4O3 [M+H]+, 355; found 355. 1H NMR (600 MHz, DMSO-D6) δ 13.0 (s, 1H), 9.69 (s, 1H), 8.91 (s, 1H), 8.35 (s, 1H), 7.88 (d, 1H, J=7.04 Hz), 7.42 (m, 1H), 7.35 (t, 1H, J=9.39 Hz), 5.89 (s, 1H), 5.54 (s, 1H), 3.44 (s, 3H), 1.96 (s, 3H).

Provenance & Evidence