Réaction #2405

Équation de réaction

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

Rendement 65.7%

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate
2. 2
   LavageThe ethyl acetate layer is washed
3. 3
   Autredried
4. 4
   Autreevaporated
5. 5
   Autreto remove the solvent
6. 6
   AutreThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1)
7. 7
   Autrerecrystallized from hexane/ethyl acetate

Mode opératoire

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).

Source