Reaction #2405

Reaction equation

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

Yield 65.7%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe ethyl acetate layer is washed
3. 3
   Otherdried
4. 4
   Otherevaporated
5. 5
   Otherto remove the solvent
6. 6
   OtherThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1)
7. 7
   Otherrecrystallized from hexane/ethyl acetate

Procedure

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