Réaction #2391

Équation de réaction

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

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

Rendement 118.4%

Solvants

trifluoroacetic anhydride

methylene chloride

Conditions de réaction

Traitement

1. 1
   Autrethe mixture is evaporated
2. 2
   Autreto remove the solvent
3. 3
   workup.DISSOLUTIONThe residue is dissolved in methanol/triethylamine (1:1) (20 ml)
4. 4
   Concentrationconcentrated to dryness under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue is dissolved in chloroform
6. 6
   Lavagewashed with saturated aqueous ammonium chloride solution and brine
7. 7
   Séchagedried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   ConcentrationThe filtrate is concentrated under reduced pressure

Mode opératoire

A solution of 4-tert-butyl-N-{6-[2-(5-methylsulfinylpyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (471 mg) in trifluoroacetic anhydride (5 ml) and methylene chloride (5 ml) is refluxed for 30 minutes, and the mixture is evaporated to remove the solvent. The residue is dissolved in methanol/triethylamine (1:1) (20 ml), and concentrated to dryness under reduced pressure. The residue is dissolved in chloroform, washed with saturated aqueous ammonium chloride solution and brine, dried over sodium sulfate, and filtered. The filtrate is concentrated under reduced pressure to give 4-tert-butyl-N-{6-[2-(5-mercaptopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide as pale yellow foam (529 mg).

Source