Potassium Carbonate → HCID 178493017, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of the 2-fluoro-6-({2-{[4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)phenyl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzamide (15.7 g, 23.4 mmol) in methanol (250 mL) and tetrahydrofuran (125 ml) was added K2CO3 (32.3g 234 mmol in 125 ml of water), The reaction mixture was stirred at 85° C. for 6 hours. The organic layer was subsequently washed with water and brine, dried over sodium sulfate, filtered, stripped onto celite, and purified by chromatography on SiO2 (400 g SiO2, 0% to 10% MeOH/CH2CL2 with 0.1% added NH3) to afford the 2-fluoro-6-[(2-{[4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)phenyl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]benzamide (11.2 g, 92%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.01 (d, J=6.59 Hz, 6 H), 2.59 (d, J=3.85 Hz, 4 H), 2.67 (m, J=6.41 Hz, 1 H), 3.10 (br. s., 4 H), 3.81 (s, 3H), 6.22 (s., 1 H), 6.47 (d, J=8.79 Hz, 1 H), 6.63 (d, J=1.28 Hz, 1 H), 6.89-6.98 (m, 2 H), 7.36-7.46 (m, 2 H), 7.90 (d, J=8.61 Hz, 1 H), 8.02 (s., 1 H), 8.10 (s, 1 H), 8.50 (d, J=8.42 Hz, 1 H), 10.47 (s, 1 H), 11.31 (s., 1 H). MS(ESI): m/z 519 (M+1)+.

Provenance & Evidence