تفاعل #2383

معادلة التفاعل

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

المردود 92.7%

المذيبات

dimethylformamide

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooling
2. 2
   workup.STIRRINGthe mixture is stirred at the same temperature for one hour
3. 3
   استخلاصextracted with ethyl acetate
4. 4
   غسيلThe ethyl acetate layer is washed
5. 5
   أخرىdried
6. 6
   أخرىevaporated
7. 7
   أخرىto remove the solvent
8. 8
   أخرىThe residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate=3:1)
9. 9
   أخرىcrystallized from ethyl acetate/diisopropyl ether

الإجراء التجريبي

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 ).

المصدر