反应详情

A mixture of 4′-({7-butyl-4-[trans-4-(2-hydroxy-1-methylpropoxy)cyclohexyl]-5-oxo-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile (0.66 g), 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (0.76 g) and acetonitrile (20 mL) was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution and sodium thiosulfate were added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr, and 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. The obtained residue was dissolved in tetrahydrofuran (15 mL), and methylmagnesium bromide (1.0 M tetrahydrofuran solution, 2.4 mL) was added at 0° C. The reaction mixture was warmed to 0° C., and stirred for 6 hr. 1 N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with 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 obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.32 g, 47%).

1. stirringthe mixture was stirred at room temperature for 2 hr
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customThe solvent was evaporated under reduced pressure
6. dissolutionThe obtained residue was dissolved in tetrahydrofuran (15 mL)
7. additionmethylmagnesium bromide (1.0 M tetrahydrofuran solution, 2.4 mL) was added at 0° C
8. temperatureThe reaction mixture was warmed to 0° C.
9. stirringstirred for 6 hr
10. addition1 N Hydrochloric acid was added to the reaction mixture
11. extractionthe mixture was extracted with ethyl acetate
12. washThe obtained ethyl acetate layer was washed with saturated brine
13. dry with materialdried over anhydrous magnesium sulfate
14. customThe solvent was evaporated under reduced pressure
15. customThe obtained residue was purified by silica gel column chromatography