Réaction #2368

Équation de réaction

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

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

Rendement 32.9%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Températurethe mixture is refluxed for four hours
2. 2
   AutreRaney-nickel is removed by filtration
3. 3
   Lavagewashed with ethanol and acetic acid
4. 4
   ConcentrationThe filtrate is concentrated under reduced pressure
5. 5
   Extractionthe residue is extracted with ethyl acetate
6. 6
   LavageThe ethyl acetate layer is washed
7. 7
   Autredried
8. 8
   Autreevaporated
9. 9
   Autreto remove the solvent
10. 10
    AutreThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=10:1)
11. 11
    Autrerecrystallized from ethyl acetate/n-hexane

Mode opératoire

A mixture of 4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(2-methylthiopyrimidin-4-yloxy)ethoxy}pyrimidin-4-yl]benzenesulfonamide (250 mg), Raney-nickel (W-2) (2 g) and ethanol (5 ml) is stirred at room temperature overnight, and the mixture is refluxed for four hours. Raney-nickel is removed by filtration, and washed with ethanol and acetic acid. The filtrate is concentrated under reduced pressure, and the residue is extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=10:1), and recrystallized from ethyl acetate/n-hexane to give 4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(pyrimidin-4-yloxy)ethoxy}pyrimidin-4-yl]benzenesulfonamide (76 mg) as crystals.

Source