2-imidazo[1,5-a]pyridin-1-yl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide → N-Tert-Butyl-2-(5,6,7,8-Tetrahydroimidazo[1,5-A]pyridin-1-Yl)-5h-Pyrrolo[2,3-B]pyrazine-7-Carboxamide

Participants

Reaction Steps

To a solution of 2-imidazo[1,5-a]pyridin-1-yl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (70 mg, 0.15 mmol) in TFA (2 mL) was added platinum(IV) oxide (7 mg, 0.03 mmol). The reaction mixture was stirred under hydrogen (balloon) for 6 h then filtered over Celite, rinsing with CH2Cl2. The filtrate was concentrated. The residue was dissolved in CH2Cl2 (3 mL) and treated with ethylenediamine (0.4 mL). The reaction mixture was stirred for 1 h then quenched with water and extracted with CH2Cl2 (2×). The combined organics were dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with 0% to 3% MeOH/CH2Cl2 (0.5% NH4OH). The appropriate fractions were combined and concentrated to afford a yellow solid which was triturated with Et2O to obtain 13 mg (26%) of 2-(5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a pale yellow solid. MS: (M+H)+=339; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 12.50 (br. s., 1H), 8.96 (s, 1H), 8.21 (s, 1H), 7.75 (s, 1H), 7.66 (s, 1H), 4.06 (t, J=5.9 Hz, 2H), 3.21 (t, J=6.2 Hz, 2H), 1.76-1.98 (m, 4H), 1.46 (s, 9H).

Provenance & Evidence