Реакция #2405

Уравнение реакции

sodium hydrogen sulfite

4-tert-butyl-N-[6-(2-hydroxyethoxy)pyrimidin-4-yl)benzenesulfonamide

N-bromosuccinimide

→

N-[5-bromo-6-(2-hydroxyethoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide

Выход 65.7%

Растворители

dimethylformamide

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/methanol=40:1)
7. 7
   Другоеrecrystallized from hexane/ethyl acetate

Методика

To a solution of 4-tert-butyl-N-[6-(2-hydroxyethoxy)pyrimidin-4-yl)benzenesulfonamide (210 mg) in dimethylformamide (4 ml) is added N-bromosuccinimide (116 mg), and the mixture is stirred at room temperature for one hour. The mixture is treated with aqueous sodium hydrogen sulfite 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/methanol=40:1), and recrystallized from hexane/ethyl acetate to give N-[5-bromo-6-(2-hydroxyethoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (169 mg).

Источник