Reacción #2405

Ecuación de reacción

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

Rendimiento 65.7%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate
2. 2
   LavadoThe ethyl acetate layer is washed
3. 3
   Otrodried
4. 4
   Otroevaporated
5. 5
   Otroto remove the solvent
6. 6
   OtroThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1)
7. 7
   Otrorecrystallized from hexane/ethyl acetate

Procedimiento

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).

Fuente