Реакция #2371

Уравнение реакции

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

Выход 75.3%

Растворители

water

Условия реакции

Обработка

1. 1
   Температураcooling
2. 2
   Температураcooling
3. 3
   workup.STIRRINGthe mixture is stirred for 30 minutes
4. 4
   Экстракцияextracted with ethyl acetate
5. 5
   ПромывкаThe ethyl acetate layer is washed
6. 6
   Другоеdried
7. 7
   Концентрированиеconcentrated to dryness under reduced pressure
8. 8
   ДругоеThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1~20:1)
9. 9
   Другоеrecrystallized from ethyl acetate/n-hexane

Методика

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.

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