Trifluoroacetic acid → HCID 73295448, compound

Participants

Reaction Steps

To a solution of N-tert-butyl-2-(2-methylpyrimidin-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (78 mg, 171 μmol) in dichloromethane (2.5 mL) was added trifluoroacetic acid (390 mg, 264 μL, 3.42 mmol) and the mixture stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the residue obtained diluted with dichloromethane (2.5 mL), methanol (1.2 mL) and ammonium hydroxide (0.35 mL) and the mixture stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo then triturated with water. The solid was collected by filtration and washed with water and ether to give N-tert-butyl-2-(2-methylpyrimidin-5-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (43 mg, 132 μmol, 77%) as a brown solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.31 (s, 1H), 9.57 (s, 1H), 8.90 (s, 2H), 7.96 (d, J=3.3, 1H), 7.92 (s, 1H), 7.53 (s, 1H), 2.46 (s, 3H), 1.32 (s, 9H); MS (EI/CI) m/z: 326.1 [M+H].

Provenance & Evidence