Diethyl Ether → HCID 73295272, compound

Participants

Reaction Steps

To a solution of N-(1-hydroxy-2-methylpropan-2-yl)-2-(5-methylpyridin-2-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (66 mg, 140 μmol) in dichloromethane (1.5 mL) was added trifluoroacetic acid (320 mg, 216 μL, 2.8 mmol) and the mixture stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo then the residue was dissolved in dichloromethane (2 mL), methanol (0.5 mL) and ammonium hydroxide (0.3 mL). After stirring at room temperature for 30 min, the mixture was concentrated in vacuo and triturated with ether and water. The yellow precipitate was collected by filtration and washed with water then ether to give N-(1-hydroxy-2-methylpropan-2-yl)-2-(5-methylpyridin-2-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (31 mg, 91.1 μmol, 65%) as a yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.38 (s, 1H), 9.86 (s, 1H), 8.39 (s, 1H), 8.12 (d, J=2.5 Hz, 1H), 8.04 (d, J=3.3 Hz, 1H), 7.95 (d, J=8.4 Hz, 1H), 7.74 (s, 1H), 7.54 (dd, J=8.6, 2.3 Hz, 1H), 5.06 (s, 1H), 3.58 (s, 2H), 2.25 (s, 3H), 1.39 (s, 6H); MS (EI/CI) m/z: 341.1 [M+H].

Provenance & Evidence