反应详情

4′-{[4-(trans-4-Hydroxycyclohexyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (4.6 g), 4-bromophenol (3.4 g) and triphenylphosphine (5.2 g) were dissolved in tetrahydrofuran (5 mL), a solution of diisopropyl azodicarboxylate (10 mL, 1.9 M toluene solution) in tetrahydrofuran (5 mL) 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 brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue obtained by purification by silica gel column chromatography was mixed with dibutyl(1-ethoxyethenyl)pentylstannane (4.0 mL), dichlorobis(triphenylphosphine)palladium (0.35 g) and tetrahydrofuran (30 mL), and the mixture was heated under reflux for 64 hr. Aqueous potassium fluoride solution was added, and the obtained mixture 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 (1.8 g, 32%).

1. extractionthe mixture was extracted with ethyl acetate
2. washThe organic layer was washed with saturated brine
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe solvent was evaporated under reduced pressure
5. customThe residue obtained by purification by silica gel column chromatography
6. temperaturethe mixture was heated
7. temperatureunder reflux for 64 hr
8. extractionthe obtained mixture was extracted with ethyl acetate
9. washThe organic 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 was purified by silica gel column chromatography