Reaktion #2383

Reaktionsgleichung

4-tert-butyl-N-{6-[2-(4-hydroxyphenoxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide

sodium hydride

tert-butyl bromoacetate

ammonium chloride

→

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

Ausbeute 92.7%

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.STIRRINGthe mixture is stirred at the same temperature for one hour
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe ethyl acetate layer is washed
5. 5
   Sonstigedried
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto remove the solvent
8. 8
   SonstigeThe residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate=3:1)
9. 9
   Sonstigecrystallized from ethyl acetate/diisopropyl ether

Vorschrift

To a solution of 4-tert-butyl-N-{6-[2-(4-hydroxyphenoxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (200 mg) in dimethylformamide (2 ml) is added sodium hydride (60% dispersion-type, 32 mg), and the mixture is stirred at room temperature for 30 minutes. To the mixture is added a solution of tert-butyl bromoacetate (77 mg) in dimethylformamide (2 ml) under ice-cooling, and the mixture is stirred at the same temperature for one hour. The reaction solution is poured into ice-water, and treated 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; hexane/ethyl acetate=3:1), and crystallized from ethyl acetate/diisopropyl ether to give tert-butyl 4-{2-(6-(4-tert-butybenzenesulfonylamino)-5-(4-methylphenyl)pyrimidin-4-yloxy)ethoxy}phenoxyacetate (225 mg ).

Quelle