Methanol → HCID 73295271, compound

Participants

Reaction Steps

To a solution of N-tert-butyl-2-(5-methylpyridin-2-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (162 mg, 356 μmol) in dichloromethane (3 mL) was added trifluoroacetic acid (813 mg, 549 μL, 7.13 mmol) and the mixture stirred at room temperature for 16 h. The mixture was then concentrated in vacuo and the residue obtained was dissolved in dichloromethane (3 mL), methanol (1 mL) and ammonium hydroxide (0.6 mL) and the mixture stirred at room temperature for 30 min. The yellow precipitate formed was collected by filtration and dried. The mother liquor was purified by chromatography (silica, 5-25% of a 1:4 methanol:dichloromethane solution in dichloromethane) and combined with the solid to give N-tert-butyl-2-(5-methylpyridin-2-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (77 mg, 237 μmol, 67%) as an off-white solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.37 (s, 1H), 9.88 (s, 1H), 8.38 (s, 1H), 8.13 (d, J=2.5 Hz, 1H), 8.04 (d, J=3.2 Hz, 1H), 7.88 (d, J=8.5 Hz, 1H), 7.74 (s, 1H), 7.51 (dd, J=8.2, 2.3 Hz, 1H), 2.25 (s, 3H), 1.47 (s, 9H); MS (EI/CI) m/z: 325.1 [M+H].

Provenance & Evidence