Reaktion #2370

Reaktionsgleichung

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

hydrochloric acid

sodium hydrogen carbonate

→

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

Ausbeute 87.0%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeis reacted at room temperature for four hours
2. 2
   Sonstigethe mixture is evaporated
3. 3
   Sonstigeto remove the solvent
4. 4
   workup.ADDITIONTo the residue are added aqueous ammonium chloride solution and ethyl acetate
5. 5
   Sonstigethe ethyl acetate layer is collected
6. 6
   WaschenThe ethyl acetate layer is washed
7. 7
   Sonstigedried
8. 8
   Sonstigeevaporated
9. 9
   Sonstigeto remove the solvent
10. 10
    SonstigeThe residue is purified by silica gel column chromatography (solvent; ethyl acetate/n-hexane=1:1~ethyl acetate)
11. 11
    Sonstigerecrystallized from ethyl acetate/n-hexane

Vorschrift

A mixture of 4-tert-butyl-N-[6-{2-(5-(1-ethoxyethenyl)pyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide (1.022 g), 10% hydrochloric acid (1 ml) and acetone (20 ml) is reacted at room temperature for four hours. The pH value of the reaction solution is adjusted to pH 6 with aqueous sodium hydrogen carbonate solution, and the mixture is evaporated to remove the solvent. To the residue are added aqueous ammonium chloride solution and ethyl acetate, and the ethyl acetate layer is collected. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; ethyl acetate/n-hexane=1:1~ethyl acetate), and recrystallized from ethyl acetate/n-hexane to give N-[6-{2-(5-acetylpyrimidin-2-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (849 mg).

Quelle