Dimethylformamide → N-tert-butyl-2-(1-methyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (150 mg, 351 mol), 1-methyl-1H-pyrazol-4-amine hydrochloride (70.3 mg, 526 mol), BINAP (10.9 mg, 17.5 mol), palladium (II) acetate (19.7 mg, 87.7 mol) and sodium tert-butoxide (84.3 mg, 877 mol) was added DMF (1 mL) and toluene (500 μL). After heating in a microwave at 140° C. for 20 min, the reaction mixture was cooled, diluted with water and extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, then dried over magnesium sulfate, and purified by chromatography (silica, 30-70% ethyl acetate in hexanes) to give N-tert-butyl-2-(1-methyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (89 mg, 201 mol, 57%) as a yellow solid. MS (EI/CI) m/z: 314.1 [M+H].

Provenance & Evidence