반응 #1806009

반응 방정식

5-(2,3-difluorobenzyl)-6-methyl-2-propylpyrimidin-4(3H)-one

3-[4′-(bromomethyl)biphenyl-2-yl]-5-(trichloromethyl)-1,2,4-oxadiazole

cesium carbonate

→

title compound

수율 20.0%

5-(2,3-difluorobenzyl)-6-methyl-3-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-2-propylpyrimidin-4(3H)-one

수율 20.0%

용매

N,N-dimethylformamide

ethyl acetate

반응 조건

후처리

1. 1
   세척washed with 1 M hydrochloric acid and saturated brine
2. 2
   건조dried over anhydrous sodium sulfate
3. 3
   기타The solvent was evaporated under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in acetone (10 mL)
5. 5
   workup.ADDITION1 M sodium hydroxide (2 mL) was added
6. 6
   workup.STIRRINGthe mixture was stirred for 30 min
7. 7
   추출extracted with ethyl acetate
8. 8
   세척The organic layer was washed with saturated brine
9. 9
   건조dried over anhydrous sodium sulfate
10. 10
    기타The solvent was evaporated under reduced pressure
11. 11
    기타The residue was purified by silica gel column chromatography

실험 절차

To a solution of 5-(2,3-difluorobenzyl)-6-methyl-2-propylpyrimidin-4(3H)-one (0.55 g) and 3-[4′-(bromomethyl)biphenyl-2-yl]-5-(trichloromethyl)-1,2,4-oxadiazole (1.03 g) in N,N-dimethylformamide (5 mL) was added cesium carbonate (0.44 g), and the mixture was stirred for 12 hr. The reaction mixture was diluted with ethyl acetate, washed with 1 M hydrochloric acid and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in acetone (10 mL), 1 M sodium hydroxide (2 mL) was added, and the mixture was stirred for 30 min. The reaction mixture was weakly acidified with 1 M hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (0.11 g, 20%) as a colorless solid.

출처