반응 #2366

반응 방정식

4-tert-butyl-N-{6-(2-hydroxyethoxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide

sodium hydride

ammonium chloride

5-bromo-2-chloropyrimidine

→

N-[-6-{2-(5-bromopyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide

수율 84.1%

용매

dimethylacetamide

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture is stirred at room temperature for 18 hours
2. 2
   추출extracted with ethyl acetate
3. 3
   세척The ethyl acetate layer is washed
4. 4
   기타dried
5. 5
   기타evaporated
6. 6
   기타to remove the solvent
7. 7
   기타The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1)
8. 8
   기타to give crude crystals, which
9. 9
   기타are recrystallized from ethyl acetate/diisopropyl ether

실험 절차

To a solution of 4-tert-butyl-N-{6-(2-hydroxyethoxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide (250 mg) in dimethylacetamide (5 ml) is added sodium hydride (60% dispersion-type, 64 mg) at room temperature, and the mixture is stirred for 20 minutes. To the reaction solution is added 5-bromo-2-chloropyrimidine (133 mg), and the mixture is stirred at room temperature for 18 hours. The reaction solution is poured into ice-water, and the mixture is neutralized 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/methanol=40:1) to give crude crystals, which are recrystallized from ethyl acetate/diisopropyl ether to give N-[-6-{2-(5-bromopyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (280 mg) as crystals.

출처