Reacción #2370

Ecuación de reacción

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

Rendimiento 87.0%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrois reacted at room temperature for four hours
2. 2
   Otrothe mixture is evaporated
3. 3
   Otroto remove the solvent
4. 4
   workup.ADDITIONTo the residue are added aqueous ammonium chloride solution and ethyl acetate
5. 5
   Otrothe ethyl acetate layer is collected
6. 6
   LavadoThe ethyl acetate layer is washed
7. 7
   Otrodried
8. 8
   Otroevaporated
9. 9
   Otroto remove the solvent
10. 10
    OtroThe residue is purified by silica gel column chromatography (solvent; ethyl acetate/n-hexane=1:1~ethyl acetate)
11. 11
    Otrorecrystallized from ethyl acetate/n-hexane

Procedimiento

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).

Fuente