Reaction #2367

Reaction equation

6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine

4-tert-amylbenzenesulfonyl chloride

potassium hydroxide

toluene

→

4-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide

Solvents

ammonium chloride

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/ethyl acetate=5:1)
7. 7
   Otherrecrystallized from hexane/ethyl acetate

Procedure

A mixture of 6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine (150 mg), 4-tert-amylbenzenesulfonyl chloride (184 mg), 96% potassium hydroxide (powder, 300 mg), tetrabutylammonium hydrogen sulfate (34 mg) and toluene (10 ml) is stirred at room temperature overnight. The mixture is diluted with saturated aqueous ammonium chloride 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/ethyl acetate=5:1), and recrystallized from hexane/ethyl acetate to give 4-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (188 mg).

Source