反应详情

2-[(trans-4-{6-[(2′-Cyanobiphenyl-4-yl)methyl]-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}cyclohexyl)oxy]-N-methoxy-N-methylacetamide (1.5 g) was dissolved in tetrahydrofuran (15 mL), 2-(1,3-dioxan-2-yl)ethylmagnesium bromide (15 mL, 0.5M tetrahydrofuran solution) was added dropwise, and the mixture was stirred at room temperature for 18 hr. The reaction mixture was added to 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was dissolved in tetrahydrofuran (5 mL) and methanol (10 mL), and sodium tetrahydroborate (0.16 g) was added at 0° C. The reaction mixture was stirred at 0° C. for 2 hr and then at room temperature for 18 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, the solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.71 g, 44%).

1. extractionthe mixture was extracted with ethyl acetate
2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution
3. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
4. customThe solvent was evaporated under reduced pressure
5. dissolutionthe residue was dissolved in tetrahydrofuran (5 mL)
6. additionmethanol (10 mL), and sodium tetrahydroborate (0.16 g) was added at 0° C
7. stirringThe reaction mixture was stirred at 0° C. for 2 hr
8. waitat room temperature for 18 hr
9. additionSaturated aqueous ammonium chloride solution was added to the reaction mixture
10. customthe solvent was evaporated under reduced pressure
11. extractionthe residue was extracted with ethyl acetate
12. washThe organic layer was washed with saturated brine
13. dry with materialdried over anhydrous magnesium sulfate
14. customThe solvent was evaporated under reduced pressure
15. customthe residue was purified by silica gel column chromatography