反応 #2382

反応方程式

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

収率 89.1%

溶媒

ethyl acetate

反応条件

後処理

1. 1
   温度is refluxed under argon atmosphere for 24 hours
2. 2
   温度After cooling
3. 3
   その他The insoluble materials are removed by filtration
4. 4
   濃縮the 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
   洗浄The aqueous layer is washed with diethyl ether
7. 7
   温度cooling
8. 8
   抽出The mixture is extracted with ethyl acetate
9. 9
   洗浄the ethyl acetate layer is washed
10. 10
    その他dried
11. 11
    その他evaporated
12. 12
    その他to remove the solvent
13. 13
    その他The residue is purified by silica gel column chromatography (solvent:chloroform:methanol=100:0~20:1)
14. 14
    その他crystallized from ethyl acetate

実験手順

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).

出典