Reaktion #2372

Reaktionsgleichung

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

Ausbeute 93.9%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture is reacted at room temperature for 0.5 hour
2. 2
   EinengenThe 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
   SonstigeThe catalyst is removed by filtration
5. 5
   Einengenthe filtrate is concentrated to dryness under reduced pressure
6. 6
   ExtraktionThe residue is extracted with ethyl acetate
7. 7
   Waschenthe ethyl acetate layer is washed
8. 8
   Sonstigedried
9. 9
   Sonstigeevaporated
10. 10
    Sonstigeto remove the solvent
11. 11
    SonstigeThe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1)
12. 12
    Sonstigerecrystallized from ethyl acetate/n-hexane

Vorschrift

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.

Quelle