反応 #2372

反応方程式

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

収率 93.9%

溶媒

methylene chloride

反応条件

後処理

1. 1
   その他the mixture is reacted at room temperature for 0.5 hour
2. 2
   濃縮The 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
   その他The catalyst is removed by filtration
5. 5
   濃縮the filtrate is concentrated to dryness under reduced pressure
6. 6
   抽出The residue is extracted with ethyl acetate
7. 7
   洗浄the ethyl acetate layer is washed
8. 8
   その他dried
9. 9
   その他evaporated
10. 10
    その他to remove the solvent
11. 11
    その他The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1)
12. 12
    その他recrystallized from ethyl acetate/n-hexane

実験手順

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.

出典