Triethylamine → (S)-tert-butyl 2-(2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)propanoate

Participants

Reaction Steps

To a solution of 2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (250 mg, 0.75 mmol) in DMF (6 mL) at room temperature was added triethylamine (0.52 mL, 3.75 mmol), (S)-tert-butyl 2-aminopropanoate hydrochloride (136 mg, 0.75 mmol) and PyBOP (429 mg, 0.83 mmol). The reaction mixture was stirred overnight then poured into EtOAc (50 mL) and washed with water (4×30 mL). The organic extracts were combined, dried (Na2SO4) and evaporated under reduced pressure. The crude residue was purified by SiO2 column chromatography (12 g, hexanes/EtOAc, 7:3 to 1:1) to give 285 mg (85%) of (S)-tert-butyl 2-(2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)propanoate as a viscous oil.

Provenance & Evidence