Methanol → Tert-butyl (5-ethynylpyridin-3-yl)carbamate

Participants

Reaction Steps

Into a reaction flask were added tert-butyl {5-[(trimethylsilyl)ethynyl]pyridin-3-yl}carbamate (2.0 g, 6.9 mmol), methanol (25 mL), and a solution of potassium carbonate (7.1 g, 52 mmol) in water (25 mL). The reaction mixture was stirred at rt overnight. The solvent was removed under vacuum and the residue was diluted with EtOAc and water. After separation, the organic layer was dried over Na2SO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired product as a white powder (1.0 g, 67%). LCMS for C12H15N2O2 (M+H)+: m/z=219.0.

Provenance & Evidence