反应详情

温度

70 °C

A mixture of 4′-{[4-(1,4-dioxaspiro[4.5]dec-8-yl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (2 g), 6N hydrochloric acid (20 mL) and tetrahydrofuran (30 mL) was stirred at 70° C. for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in methanol (30 mL), sodium borohydride (0.18 g) was added, and the mixture was stirred at room temperature for 1 hr. After evaporation of the solvent under reduced pressure, the residue was extracted with water and ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue obtained by silica gel column chromatography was dissolved in N,N-dimethylformamide (10 mL), methyl iodide (0.13 mL) and sodium hydride (0.05 g) were added, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous potassium hydrogensulfate solution and then 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 (0.21 g, 28%).

1. washwashed with saturated brine
2. dry with materialdried over anhydrous magnesium sulfate
3. customThe solvent was evaporated under reduced pressure
4. dissolutionThe obtained residue was dissolved in methanol (30 mL)
5. additionsodium borohydride (0.18 g) was added
6. stirringthe mixture was stirred at room temperature for 1 hr
7. customAfter evaporation of the solvent under reduced pressure
8. extractionthe residue was extracted with water and ethyl acetate
9. washThe obtained ethyl acetate layer was washed with saturated brine
10. dry with materialdried over anhydrous magnesium sulfate
11. customThe solvent was evaporated under reduced pressure
12. customThe residue obtained by silica gel column chromatography
13. stirringthe mixture was stirred at room temperature for 16 hr
14. washwashed with 5% aqueous potassium hydrogensulfate solution
15. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
16. customThe solvent was evaporated under reduced pressure
17. customthe residue was purified by silica gel column chromatography