Reaktion #2405

Reaktionsgleichung

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

Ausbeute 65.7%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe ethyl acetate layer is washed
3. 3
   Sonstigedried
4. 4
   Sonstigeevaporated
5. 5
   Sonstigeto remove the solvent
6. 6
   SonstigeThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1)
7. 7
   Sonstigerecrystallized from hexane/ethyl acetate

Vorschrift

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).

Quelle