Ethanol → HCID 86679637, compound

Participants

Reaction Steps

To a solution of N-{3-[(2-[(1-methyl-1H-pyrazol-4-yl)amino]-5-(pyridin-3-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]phenyl}prop-2-enamide (123 mg, 0.21 mmol) in DCM (10 mL) was added TFA (0.6 mL). The reaction solution was stirred at rt for 3 hrs. The volatiles were removed to give a residue. To the residue was added ethanol (20 mL), water (2 mL), and K2CO3 (142 mg) and the reaction mixture was stirred at rt for 1 hr. The volatiles were removed and water (10 mL) was added. The resulting solid was collected by filtration, washed with water (10 mL) and dried to give the title product (92.8 mg, 100% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.80 (br. s., 1H) 10.32 (br. s., 1H) 8.99-9.14 (m, 1H) 8.95 (d, J=1.51 Hz, 1H) 8.41 (dd, J=4.78, 1.51 Hz, 1H) 8.12 (d, J=7.55 Hz, 1H) 7.64 (br. s., 2H) 7.47 (s, 2H) 7.39 (dd, J=7.93, 4.91 Hz, 1H) 7.21 (br. s., 1H) 7.04 (br. s., 1H) 6.34-6.48 (m, 1H) 6.19-6.31 (m, 1H) 5.70-5.82 (m, 1H) 3.58 (br. s., 3H). m/z (APCI+) for C24H20N8O2 453.0 (M+H)+.

Provenance & Evidence