Reaktion #2135932

Reaktionsgleichung

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

hydroxylammonium chloride

sodium hydrogen carbonate

dimethyl sulfoxide

→

title compound

Ausbeute 48.0%

2-methyl-4-(6-methyltetrahydro-2H-pyran-3-yl)-6-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one

Ausbeute 48.0%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at 90° C. for 16 hr
2. 2
   Waschenwashed with water
3. 3
   Trocknenwith saturated brine, and dried over anhydrous magnesium sulfate
4. 4
   SonstigeThe solvent was evaporated under reduced pressure
5. 5
   workup.DISSOLUTIONthe residue was dissolved in tetrahydrofuran (5 mL)
6. 6
   workup.ADDITIONN,N′-Carbonyldiimidazole (0.073 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.062 mL) were added
7. 7
   workup.STIRRINGthe mixture was stirred at room temperature for 2 hr
8. 8
   workup.ADDITIONThe reaction mixture was diluted with ethyl acetate
9. 9
   Waschenwashed with saturated aqueous potassium hydrogensulfate solution
10. 10
    Trocknenwith saturated brine, and dried over anhydrous magnesium sulfate
11. 11
    SonstigeThe solvent was evaporated under reduced pressure
12. 12
    Sonstigethe residue was purified by silica gel column chromatography

Vorschrift

A mixture of hydroxylammonium chloride (0.39 g), sodium hydrogen carbonate (0.64 g) and dimethyl sulfoxide (5 mL) was stirred at 40° C. for 30 min, 4′-{[2-methyl-4-(6-methyltetrahydro-2H-pyran-3-yl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (0.18 g) was added, and the mixture was stirred at 90° C. for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was dissolved in tetrahydrofuran (5 mL). N,N′-Carbonyldiimidazole (0.073 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.062 mL) were added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated 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 amorphous solid (0.097 g, 47%).

Quelle