반응 #2386

반응 방정식

ammonium chloride

4-tert-butyl-N-[6-{2-(5-formylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide

sodium borohydride

→

4-tert-butyl-N-[6-{2-(5-hydroxymethylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide

수율 66.9%

용매

tetrahydrofuran isopropanol

반응 조건

후처리

1. 1
   온도cooling
2. 2
   기타the mixture is reacted for two hours
3. 3
   추출extracted with ethyl acetate
4. 4
   세척The ethyl acetate layer is washed
5. 5
   기타dried
6. 6
   기타evaporated
7. 7
   기타to remove the solvent
8. 8
   기타The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=200:1~50:1)
9. 9
   기타crystallized from diethyl ether

실험 절차

To a solution of 4-tert-butyl-N-[6-{2-(5-formylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide (143 mg) in tetrahydrofuran-isopropanol (4 ml-4 ml) is added sodium borohydride (13 mg) under ice-cooling, and the mixture is reacted for two hours. The mixture is treated with aqueous ammonium chloride solution, and extracted with ethyl acetate. 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=200:1~50:1), and crystallized from diethyl ether to give 4-tert-butyl-N-[6-{2-(5-hydroxymethylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide (96 mg).

출처