反应详情

温度

0 °C

To a solution of 5-trimethylsilanylethynyl-pyridin-2-ylamine (example D.1 method 1 step 1) (32.08 g, 169 mmol) in THF (150 mL) and MeOH (350 mL) at 0° C. was added K2CO3 (2.33 g, 10 mol %) and the mixture was stirred at 0° C. for 5 h. Diluted with ice water (500 mL), extracted with TBME (3×500 mL), washed the combined organic layers with brine, dried over MgSO4. Removal of the solvent in vacuum 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. Evaporation of the mother liquor followed by silica gel column chromatography gave a brown solid which was triturated with ether and n-heptane to give a second crop of the title compound (3.26 g, 16%) as a light brown solid. MS (EI) 118.1 [(M)+]; mp 143° C.

1. customat 0° C.
2. extractionextracted with TBME (3×500 mL)
3. washwashed the combined organic layers with brine
4. dry with materialdried over MgSO4
5. customRemoval of the solvent in vacuum
6. waitleft a dark brown solid, which
7. dissolutionwas dissolved in hot ethyl acetate
8. customprecipitated with n-heptane trituration