反应详情

温度

0 °C

Dissolve 2,6-diaminopyridine (9.822 g, 90 mmol) in dioxane (100 mL) and cool to 0° C. Add acetyl chloride (2.355 g, 2.1 mL, 30 mmol) slowly and stir for 1 hr. at 0° C. Remove the ice bath and stir at room temperature overnight. Quench the reaction mixture with saturated NaHCO3 solution, extract with ethylacetate three times. Combine the organic layers, dry over Na2SO4, filter, and concentrate to give a solid. Chromatography on silica gel, eluting with a gradient of 60–70% ethylacetate in hexanes affords the title intermediate (3.45 g, 76%): mass spectrum (ion spray): mz/z=152.1 (M+1); 1H NMR (CDCl3, ppm): 7.49 (m, 3H), 6.28 (d, 1H), 4.31 (s, br, 2H), 2.19 (s, 3H).

1. customat 0° C
2. customRemove the ice bath
3. customQuench the reaction mixture with saturated NaHCO3 solution
4. extractionextract with ethylacetate three times
5. dry with materialCombine the organic layers, dry over Na2SO4
6. filtrationfilter
7. concentrationconcentrate
8. customto give a solid
9. washChromatography on silica gel, eluting with a gradient of 60–70% ethylacetate in hexanes