تفاعل #2392

معادلة التفاعل

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

المذيبات

ammonium chloride

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture is cooled to room temperature
2. 2
   استخلاصThe mixture is extracted with ethyl acetate
3. 3
   غسيلthe organic layer is washed with water (twice) and brine
4. 4
   تجفيفdried over sodium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزThe filtrate is concentrated under reduced pressure
7. 7
   أخرىthe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1)
8. 8
   أخرىrecrystallized from tetrahydrofuran/ethyl acetate

الإجراء التجريبي

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.

المصدر