反应详情

To a mixture of 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 g), rhodium(I) acetate (0.028 g) and toluene (70 mL) was added dropwise a solution (10 mL) of 3-ethoxy-2-methyl-3-oxopropane-1-diazonium (5.5 mL) in toluene at 80° C., and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was concentrated, and the obtained residue was purified by silica gel column chromatography. The obtained residue was dissolved in tetrahydrofuran (20 mL) and methanol (20 mL), and 1N aqueous sodium hydroxide solution (20 mL) was added. The reaction mixture was stirred for 1 hr, 1N aqueous hydrochloric acid solution was added, 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 (4.1 g, 89%).

1. concentrationThe reaction mixture was concentrated
2. customthe obtained residue was purified by silica gel column chromatography
3. dissolutionThe obtained residue was dissolved in tetrahydrofuran (20 mL)
4. additionmethanol (20 mL), and 1N aqueous sodium hydroxide solution (20 mL) was added
5. stirringThe reaction mixture was stirred for 1 hr
6. addition1N aqueous hydrochloric acid solution was added
7. extractionthe mixture was extracted with ethyl acetate
8. washThe obtained ethyl acetate layer was washed with saturated brine
9. dry with materialdried over anhydrous magnesium sulfate
10. customThe solvent was evaporated under reduced pressure
11. customThe obtained residue was purified by silica gel column chromatography