Reaction #2384

Reaction equation

tert-butyl 4-{2-{6-(4-tert-butylbenzenesulfonylamino)-5-(4-methylphenyl)pyrimidin-4-yloxy]ethoxy}phenoxyacetate

anisole

trifluoroacetic acid

→

4-{2-[6-(4-tert-butylbenzenesulfonylamino)-5-(4-methylphenyl)pyrimidin-4-yl-oxy]ethoxy}phenoxyacetic acid

Solvents

dichloromethane

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   Washwashed with water
3. 3
   Extractionextracted with 10% aqueous sodium hydroxide solution
4. 4
   WashThe aqueous layer is washed with chloroform
5. 5
   Temperaturecooling
6. 6
   ExtractionThe mixture is extracted with ethyl acetate
7. 7
   Washthe extract is washed
8. 8
   Otherdried
9. 9
   Otherevaporated
10. 10
    Otherto remove the solvent
11. 11
    OtherThe residue is crystallized from ethyl acetate/diisopropyl ether

Procedure

To a solution of tert-butyl 4-{2-{6-(4-tert-butylbenzenesulfonylamino)-5-(4-methylphenyl)pyrimidin-4-yloxy]ethoxy}phenoxyacetate (1.25 g) in dichloromethane (120 ml) are added anisole (2.09 g) and trifluoroacetic acid (20 ml) under ice-cooling. The mixture is stirred at room temperature for five hours, washed with water, and extracted with 10% aqueous sodium hydroxide solution. The aqueous layer is washed with chloroform, and acidified with 10% hydrochloric acid under ice-cooling. The mixture is extracted with ethyl acetate, and the extract is washed, dried, and evaporated to remove the solvent. The residue is crystallized from ethyl acetate/diisopropyl ether to give 4-{2-[6-(4-tert-butylbenzenesulfonylamino)-5-(4-methylphenyl)pyrimidin-4-yl-oxy]ethoxy}phenoxyacetic acid (1.14 9).

Source