تفاعل #2396

معادلة التفاعل

hydrochloric acid

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

potassium carbonate

5-bromo-2-chloropyrimidine

→

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

المردود 92.0%

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with ethyl acetate
2. 2
   غسيلThe organic layer is washed with water and brine
3. 3
   تجفيفdried over anhydrous sodium sulfate
4. 4
   أخرىevaporated
5. 5
   أخرىto remove the solvent
6. 6
   أخرىThe oily residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=50:1)
7. 7
   أخرىthe fractions are evaporated
8. 8
   أخرىto remove the solvent
9. 9
   أخرىThe resulting crude crystals are recrystallized from methylene chloride/isopropyl ether

الإجراء التجريبي

To a solution of 4-tert-butyl-N-{6-[2-(5-hydroxypyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (200 mg) in dimethylformamide (4 ml)is added potassium carbonate (154 mg), 5-bromo-2-chloropyrimidine (216 mg), and the mixture is stirred at 50° C. for two hours. The reaction mixture is acdified with cold hydrochloric acid, and extracted with ethyl acetate. The organic layer is washed with water and brine, and dried over anhydrous sodium sulfate, and evaporated to remove the solvent. The oily residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=50:1), and the fractions are evaporated to remove the solvent. The resulting crude crystals are recrystallized from methylene chloride/isopropyl ether to give 4-tert-butyl-N-{6-[2-(5-(5-bromopyrimidin-2-yloxy)pyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (238 mg) as colorless needles.

المصدر