반응 #2382

반응 방정식

4-tert-butyl-N-{6-[2-(4-cyanophenoxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzensulfonamide

tributyltin azide

toluene

potassium fluoride

→

4-tert-butyl-N-{5-(4-methylphenyl)-6-[2-(4-(5-tetrazolyl)phenoxy)ethoxy]-pyrimidin-4-yl}benzensulfonamide

수율 89.1%

용매

ethyl acetate

반응 조건

후처리

1. 1
   온도is refluxed under argon atmosphere for 24 hours
2. 2
   온도After cooling
3. 3
   기타The insoluble materials are removed by filtration
4. 4
   농축the ethyl acetate layer is concentrated to dryness under reduced pressure
5. 5
   workup.ADDITIONTo the residue are added 10% aqueous sodium hydroxide solution and diethyl ether
6. 6
   세척The aqueous layer is washed with diethyl ether
7. 7
   온도cooling
8. 8
   추출The mixture is extracted with ethyl acetate
9. 9
   세척the ethyl acetate layer is washed
10. 10
    기타dried
11. 11
    기타evaporated
12. 12
    기타to remove the solvent
13. 13
    기타The residue is purified by silica gel column chromatography (solvent:chloroform:methanol=100:0~20:1)
14. 14
    기타crystallized from ethyl acetate

실험 절차

A mixture of 4-tert-butyl-N-{6-[2-(4-cyanophenoxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzensulfonamide (1.31 g), tributyltin azide (1.60 g) and toluene (13 ml) is refluxed under argon atmosphere for 24 hours. After cooling, ethyl acetate and 10% aqueous potassium fluoride solution are added to the reaction solution. The insoluble materials are removed by filtration, and the ethyl acetate layer is concentrated to dryness under reduced pressure. To the residue are added 10% aqueous sodium hydroxide solution and diethyl ether, and the mixture is stirred at room temperature for 20 minutes. The aqueous layer is washed with diethyl ether, and acidified with 10% hydrochloric acid under ice-cooling. The mixture is extracted with ethyl acetate, and the ethyl acetate layer is washed, dried and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent:chloroform:methanol=100:0~20:1), and crystallized from ethyl acetate to give 4-tert-butyl-N-{5-(4-methylphenyl)-6-[2-(4-(5-tetrazolyl)phenoxy)ethoxy]-pyrimidin-4-yl}benzensulfonamide (1.26 g).

출처