Reaction #2368

Reaction equation

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

→

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

Yield 32.9%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturethe mixture is refluxed for four hours
2. 2
   OtherRaney-nickel is removed by filtration
3. 3
   Washwashed 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
   WashThe ethyl acetate layer is washed
7. 7
   Otherdried
8. 8
   Otherevaporated
9. 9
   Otherto remove the solvent
10. 10
    OtherThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=10:1)
11. 11
    Otherrecrystallized from ethyl acetate/n-hexane

Procedure

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