Reaction #606825

Reaction equation

4′-{[4-(trans-3-acetylcyclobutyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

hydrogen peroxide water

sodium hydrogen carbonate

sodium thiosulfate

trifluoroacetic acid anhydride

→

title compound

Yield 23.0%

4′-{[4-(trans-3-hydroxycyclobutyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

Yield 23.0%

Solvents

chloroform

Conditions

Workup

1. 1
   Otherat room temperature
2. 2
   Extractionthe mixture was extracted with ethyl acetate
3. 3
   WashThe organic layer was washed with saturated brine
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   OtherThe solvent was evaporated under reduced pressure
6. 6
   workup.DISSOLUTIONThe obtained residue was dissolved in tetrahydrofuran (10 mL)
7. 7
   workup.ADDITIONmethanol (10 mL), 1N aqueous sodium hydroxide solution (5 mL) was added
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature for 30 min
9. 9
   workup.ADDITION1N Aqueous hydrochloric acid solution was added to the reaction mixture
10. 10
    Extractionthe mixture was extracted with ethyl acetate
11. 11
    WashThe ethyl acetate layer was washed with saturated brine
12. 12
    Dryingdried over anhydrous magnesium sulfate
13. 13
    OtherThe solvent was evaporated under reduced pressure
14. 14
    OtherThe obtained residue was purified by silica gel column chromatography

Procedure

To a mixture of 4′-{[4-(trans-3-acetylcyclobutyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (1.3 g), 30% hydrogen peroxide water (3.5 g) and chloroform (20 mL) was gradually added trifluoroacetic acid anhydride (7.7 mL) at room temperature, and the reaction mixture was warmed to 60° C. and stirred for 24 hr. Saturated aqueous sodium hydrogen carbonate and sodium thiosulfate were added to the reaction mixture, 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 obtained residue was dissolved in tetrahydrofuran (10 mL) and methanol (10 mL), 1N aqueous sodium hydroxide solution (5 mL) was added, and the mixture was stirred at room temperature for 30 min. 1N Aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The 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 (0.28 g, 23%).

Source