Potassium Carbonate → 5-Ethynylpyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-trimethylsilanylethynyl-pyridin-2-ylamine (32.1 g, 169 mmol) in THF (150 mL) and methanol (350 mL) at 0° C. was added potassium carbonate (2.33 g, 16.9 mmol) and the mixture was stirred at 0° C. for 5 h. It was diluted with ice water (500 mL), extracted with tert-butylmethylether (3×500 mL), washed the combined organic layers with brine and dried over magnesium sulfate. Concentration left a dark brown solid, which was dissolved in hot ethyl acetate and precipitated with n-heptane trituration to give the 5-ethynyl-pyridin-2-ylamine (14.61 g, 73%) as a light brown solid. MS: m/e=118.1 [M+H]+.

Provenance & Evidence