تفاعل #2371

معادلة التفاعل

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

المردود 75.3%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooling
2. 2
   درجة الحرارةcooling
3. 3
   workup.STIRRINGthe mixture is stirred for 30 minutes
4. 4
   استخلاصextracted with ethyl acetate
5. 5
   غسيلThe ethyl acetate layer is washed
6. 6
   أخرىdried
7. 7
   تركيزconcentrated to dryness under reduced pressure
8. 8
   أخرىThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1~20:1)
9. 9
   أخرىrecrystallized from ethyl acetate/n-hexane

الإجراء التجريبي

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.

المصدر