Реакция #2367

Уравнение реакции

6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine

4-tert-amylbenzenesulfonyl chloride

potassium hydroxide

toluene

→

4-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide

Растворители

ammonium chloride

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ethyl acetate
2. 2
   ПромывкаThe ethyl acetate layer is washed
3. 3
   Другоеdried
4. 4
   Другоеevaporated
5. 5
   Другоеto remove the solvent
6. 6
   ДругоеThe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=5:1)
7. 7
   Другоеrecrystallized from hexane/ethyl acetate

Методика

A mixture of 6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine (150 mg), 4-tert-amylbenzenesulfonyl chloride (184 mg), 96% potassium hydroxide (powder, 300 mg), tetrabutylammonium hydrogen sulfate (34 mg) and toluene (10 ml) is stirred at room temperature overnight. The mixture is diluted with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=5:1), and recrystallized from hexane/ethyl acetate to give 4-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (188 mg).

Источник