反応 #2371

反応方程式

sodium borohydride

N-[6-{2-(5-acetylpyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide

tetrahydrofuran

isopropyl alcohol

sodium borohydride

→

4-tert-butyl-N-[6-{2-(5-(1-hydroxyethyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide

収率 75.3%

溶媒

water

反応条件

後処理

1. 1
   温度cooling
2. 2
   温度cooling
3. 3
   workup.STIRRINGthe mixture is stirred for 30 minutes
4. 4
   抽出extracted with ethyl acetate
5. 5
   洗浄The ethyl acetate layer is washed
6. 6
   その他dried
7. 7
   濃縮concentrated to dryness under reduced pressure
8. 8
   その他The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1~20:1)
9. 9
   その他recrystallized from ethyl acetate/n-hexane

実験手順

To a mixture of N-[6-{2-(5-acetylpyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (756 mg), tetrahydrofuran (10 ml) and isopropyl alcohol (10 ml) is added with stirring sodium borohydride (48 mg) under ice-cooling, and the mixture is stirred for 40 minutes under ice-cooling. To the reaction solution is further added sodium borohydride (14 mg), and the mixture is stirred for 30 minutes. The mixture is diluted with water, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and concentrated to dryness under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1~20:1), and recrystallized from ethyl acetate/n-hexane to give 4-tert-butyl-N-[6-{2-(5-(1-hydroxyethyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide (571 mg) as crystals.

出典