Réaction #2371

Équation de réaction

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

Rendement 75.3%

Solvants

water

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   Températurecooling
3. 3
   workup.STIRRINGthe mixture is stirred for 30 minutes
4. 4
   Extractionextracted with ethyl acetate
5. 5
   LavageThe ethyl acetate layer is washed
6. 6
   Autredried
7. 7
   Concentrationconcentrated to dryness under reduced pressure
8. 8
   AutreThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1~20:1)
9. 9
   Autrerecrystallized from ethyl acetate/n-hexane

Mode opératoire

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.

Source