반응 #2372

반응 방정식

4-tert-butyl-N-[6-{2-(5-(1-hydroxyethyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide

thionyl chloride

→

4-tert-butyl-N-[6-{2-(5-ethylpyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide

수율 93.9%

용매

methylene chloride

반응 조건

후처리

1. 1
   기타the mixture is reacted at room temperature for 0.5 hour
2. 2
   농축The reaction solution is concentrated to dryness under reduced pressure
3. 3
   workup.ADDITIONto the residue are added 10% palladium-carbon (30 mg), triethylamine (76 mg) and ethanol (3 ml)
4. 4
   기타The catalyst is removed by filtration
5. 5
   농축the filtrate is concentrated to dryness under reduced pressure
6. 6
   추출The residue is extracted with ethyl acetate
7. 7
   세척the ethyl acetate layer is washed
8. 8
   기타dried
9. 9
   기타evaporated
10. 10
    기타to remove the solvent
11. 11
    기타The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1)
12. 12
    기타recrystallized from ethyl acetate/n-hexane

실험 절차

To a solution of 4-tert-butyl-N-[6-{2-(5-(1-hydroxyethyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide (150 mg) in methylene chloride (3 ml) is added thionyl chloride (90 mg), and the mixture is reacted at room temperature for 0.5 hour. The reaction solution is concentrated to dryness under reduced pressure, and to the residue are added 10% palladium-carbon (30 mg), triethylamine (76 mg) and ethanol (3 ml), and the mixture is stirred at room temperature for two hours under hydrogen atmosphere (1 atm). The catalyst is removed by filtration, and the filtrate is concentrated to dryness under reduced pressure. The residue is extracted with ethyl acetate, and the ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1), and recrystallized from ethyl acetate/n-hexane to give 4-tert-butyl-N-[6-{2-(5-ethylpyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide (137 mg) as crystals.

출처