Réaction #2392

Équation de réaction

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

Solvants

ammonium chloride

Conditions de réaction

Traitement

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

Mode opératoire

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