Reaktion #2394

Reaktionsgleichung

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

potassium carbonate

methanol

→

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

Ausbeute 85.3%

Lösungsmittel

ammonium chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe organic layer is washed with water and brine
3. 3
   Trocknendried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   EinengenThe filtrate is concentrated under reduced pressure
6. 6
   Sonstigethe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=30:1)

Vorschrift

A mixture of 4-tert-butyl-N-{6-[2-(5-trimethylsilylethynylpyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (667 mg), potassium carbonate (299 mg) and dry methanol (13 ml) is stirred at 0° C. for two hours, and diluted with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer is washed with water and brine, dried over sodium sulfate, and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=30:1) to give 4-tert-butyl-N-{6-[2-(5-ethynylpyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}-benzenesulfonamide (502 mg) as colorless crystalline powder.

Quelle