반응 #1976636

반응 방정식

6-ethyl-3-(2-pyridin-2-ylethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

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

potassium carbonate

N,N-dimethylformamide

→

title compound

수율 14.0%

6-ethyl-1-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-3-(2-pyridin-2-ylethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

수율 14.0%

용매

ethyl acetate

반응 조건

후처리

1. 1
   세척washed successively with water and saturated brine
2. 2
   건조dried over anhydrous magnesium sulfate
3. 3
   기타The solvent was evaporated under reduced pressure
4. 4
   기타The obtained residue was purified by silica gel column chromatography
5. 5
   workup.DISSOLUTIONdissolved in tetrahydrofuran (5 mL)
6. 6
   workup.ADDITION1N Aqueous sodium hydroxide solution (5 mL) was added
7. 7
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hr
8. 8
   추출the mixture was extracted with ethyl acetate
9. 9
   세척The obtained ethyl acetate layer was washed with saturated brine
10. 10
    건조dried over anhydrous magnesium sulfate
11. 11
    기타The solvent was evaporated under reduced pressure
12. 12
    기타The residue was purified by silica gel column chromatography

실험 절차

A mixture of 6-ethyl-3-(2-pyridin-2-ylethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.4 g), 3-[4′-(bromomethyl)biphenyl-2-yl]-5-(trichloromethyl)-1,2,4-oxadiazole (0.58 g), potassium carbonate (0.18 g) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed successively with water and 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 and dissolved in tetrahydrofuran (5 mL) and methanol (5 mL). 1N Aqueous sodium hydroxide solution (5 mL) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was adjusted to pH 7 with water and 1N hydrochloric acid, 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 residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.1 g, 14%).

출처