Reaktion #2371

Reaktionsgleichung

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

Ausbeute 75.3%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   Temperaturcooling
3. 3
   workup.STIRRINGthe mixture is stirred for 30 minutes
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe ethyl acetate layer is washed
6. 6
   Sonstigedried
7. 7
   Einengenconcentrated to dryness under reduced pressure
8. 8
   SonstigeThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1~20:1)
9. 9
   Sonstigerecrystallized from ethyl acetate/n-hexane

Vorschrift

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.

Quelle