Methanol → HCID 73295274, compound

Participants

Reaction Steps

To a solution of N-isopropyl-2-(5-methylpyridin-2-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (90 mg, 204 μmol) in dichloromethane (2.5 mL) was added trifluoroacetic acid (466 mg, 315 μL, 4.09 mmol) and stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo then the residue obtained was dissolved in dichloromethane (3 mL), methanol (1.5 mL) and ammonium hydroxide (0.45 mL). After 3 h at room temperature, the mixture was concentrated in vacuo then triturated with water and ether. The solid was collected by filtration to give N-isopropyl-2-(5-methylpyridin-2-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (23 mg, 74.1 μmol, 36%) as an off white solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.40 (s, 1H), 9.92 (s, 1H), 8.43 (s, 1H), 8.14 (s, 1H), 8.09 (d, J=3.2, 1 H), 7.86 (s, 1H), 7.85 (d, J=15.1 Hz, 1H), 7.55 (dd, J=8.5, 2.3 Hz, 1H), 4.16 (m, 1H), 2.26 (s, 3H), 1.25 (d, J=6.5, 6 H); MS (EI/CI) m/z: 311.1 [M+H].

Provenance & Evidence