Reaction #2392

Reaction equation

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

Solvents

ammonium chloride

Conditions

Workup

1. 1
   TemperatureThe mixture is cooled to room temperature
2. 2
   ExtractionThe mixture is extracted with ethyl acetate
3. 3
   Washthe organic layer is washed with water (twice) and brine
4. 4
   Dryingdried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   ConcentrationThe filtrate is concentrated under reduced pressure
7. 7
   Otherthe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1)
8. 8
   Otherrecrystallized from tetrahydrofuran/ethyl acetate

Procedure

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.

Source