반응 #2392

반응 방정식

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

1,3-dimethyl-2-imidazolidinone

→

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

용매

ammonium chloride

반응 조건

후처리

1. 1
   온도The mixture is cooled to room temperature
2. 2
   추출The mixture is extracted with ethyl acetate
3. 3
   세척the organic layer is washed with water (twice) and brine
4. 4
   건조dried over sodium sulfate
5. 5
   여과filtered
6. 6
   농축The filtrate is concentrated under reduced pressure
7. 7
   기타the residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1)
8. 8
   기타recrystallized from tetrahydrofuran/ethyl acetate

실험 절차

A mixture of 4-tert-butyl-N-{6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (1.00 g), zinc cyanide (784 mg), tetrakis(triphenylphosphine)palladium (250 mg) and 1,3-dimethyl-2-imidazolidinone (40 ml) is stirred at 80° C. for 6 hours under argon atmosphere. The mixture is cooled to room temperature, and diluted with saturated aqueous ammonium chloride solution. The mixture is extracted with ethyl acetate, and the organic layer is washed with water (twice) 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=10:1) and recrystallized from tetrahydrofuran/ethyl acetate to give 4-tert-butyl-N-{6-[2-(5-cyanopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (590 mg) as colorless crystalline powder.

출처