تفاعل #2382

معادلة التفاعل

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

المردود 89.1%

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةis refluxed under argon atmosphere for 24 hours
2. 2
   درجة الحرارةAfter cooling
3. 3
   أخرىThe insoluble materials are removed by filtration
4. 4
   تركيزthe 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
   غسيلThe aqueous layer is washed with diethyl ether
7. 7
   درجة الحرارةcooling
8. 8
   استخلاصThe mixture is extracted with ethyl acetate
9. 9
   غسيلthe ethyl acetate layer is washed
10. 10
    أخرىdried
11. 11
    أخرىevaporated
12. 12
    أخرىto remove the solvent
13. 13
    أخرىThe residue is purified by silica gel column chromatography (solvent:chloroform:methanol=100:0~20:1)
14. 14
    أخرىcrystallized from ethyl acetate

الإجراء التجريبي

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).

المصدر