Dimethylamine → HCID 89630042, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-(3-aminophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (100 mg, 0.354 mmol) in THF (2 mL) was added (E)-4-bromobut-2-enoyl bromide (0.400 mmol) and the resulting reaction mixture was stirred for 1 hour at 0° C. Dimethylamine (0.886 mL, 1.77 mmol, 2 M in THF) was then added and the reaction mixture was sealed and stirred overnight. Water (10 mL) was added and the mixture was extracted with ethyl acetate (×3). The combined organic fractions were dried over sodium sulfate, filtered and concentrated under reduced pressure. The reaction 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 saturated aqueous sodium bicarbonate and the mixture was extracted with ethyl acetate (×5). The combined organic fractions were dried over sodium sulfate, filtered and concentrated under reduced pressure to give ethyl-4-(3-{[(2E)-4-(dimethylamino)but-2-enoyl]amino}phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C21H24N5O3 [M+H]+: 394, found 394. 1H NMR (600 MHz, DMSO-D6) δ 13.0 (s, 1H), 10.2 (s, 1H), 8.91 (s, 1H), 8.31 (s, 1H), 8.00 (s, 1H), 7.78 (d, 1H, J=8.21 Hz), 7.41 (t, 1H, J=8.21 Hz), 7.31 (d, 1H, J=7.63 Hz), 6.73 (dt, 1H, J=15.3, 5.87 Hz), 6.27 (d, 1H, J=15.3 Hz), 3.84 (q, 2H, J=7.04 Hz), 3.06 (d, 2H, J=5.87 Hz), 2.18 (s, 6H), 0.83 (t, 3H, J=7.04 Hz).

Provenance & Evidence