Triethylamine → (S)-2-cyclopropyl-N-(1-(dimethylamino)-1-oxopropan-2-yl)-5-((2-(trimethyl-silyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Steps

To a solution of (S)-2-(2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)propanoic acid (253 mg, 0.63 mmol), triethylamine (0.44 mL, 3.13 mmol), and dimethylamine hydrochloride (102 mg, 1.25 mmol) in DMF (5 mL) at room temperature was added PyBOP (358 mg, 0.69 mmol). The reaction mixture was stirred overnight then diluted with EtOAc (50 mL) and washed with water (4×25 mL). The organic extracts were combined and dried (Na2SO4) then evaporated under vacuum. The crude residue was purified by SiO2 chromatography (24 g, hexanes:EtOAc, 3:7) to give 190 mg (70%) of (S)-2-cyclopropyl-N-(1-(dimethylamino)-1-oxopropan-2-yl)-5-((2-(trimethyl-silyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide as a colorless viscous oil.

Provenance & Evidence