反応 #2386

反応方程式

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

収率 66.9%

溶媒

tetrahydrofuran isopropanol

反応条件

後処理

1. 1
   温度cooling
2. 2
   その他the mixture is reacted for two hours
3. 3
   抽出extracted with ethyl acetate
4. 4
   洗浄The ethyl acetate layer is washed
5. 5
   その他dried
6. 6
   その他evaporated
7. 7
   その他to remove the solvent
8. 8
   その他The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=200:1~50:1)
9. 9
   その他crystallized from diethyl ether

実験手順

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).

出典