反应详情

Methyl 2-chloro-6-(1-ethoxyvinyl)pyrimidine-4-carboxylate (3.5 g, 14.4 mmol) was dissolved in MeOH (35 mL), DMF (24.50 mL) and water (3.5 mL) by careful heating. The mixture was cooled on an ice-bath and sodium borohydride (1.47 g, 38.9 mmol) was added in small portions (about 50 mg every 5 min) keeping the temperature below 5° C. After 3.5 h acetic acid (3.96 mL, 69.23 mmol) was added. MeOH was evaporated and water was added. The mixture was extracted with diisopropyl ether (3×50 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The product was purified by column chromatography on silica eluting with a gradient of EtOAc in heptane to give the title compound as a solid 1.8 g (58%).

1. temperatureThe mixture was cooled on an ice-bath
2. customthe temperature below 5° C
3. customMeOH was evaporated
4. additionwater was added
5. extractionThe mixture was extracted with diisopropyl ether (3×50 mL)
6. washThe organic layer was washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe product was purified by column chromatography on silica eluting with a gradient of EtOAc in heptane