Reacción #2367

Ecuación de reacción

6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine

4-tert-amylbenzenesulfonyl chloride

potassium hydroxide

toluene

→

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

Disolventes

ammonium chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate
2. 2
   LavadoThe ethyl acetate layer is washed
3. 3
   Otrodried
4. 4
   Otroevaporated
5. 5
   Otroto remove the solvent
6. 6
   OtroThe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=5:1)
7. 7
   Otrorecrystallized from hexane/ethyl acetate

Procedimiento

A mixture of 6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine (150 mg), 4-tert-amylbenzenesulfonyl chloride (184 mg), 96% potassium hydroxide (powder, 300 mg), tetrabutylammonium hydrogen sulfate (34 mg) and toluene (10 ml) is stirred at room temperature overnight. The mixture is diluted with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=5:1), and recrystallized from hexane/ethyl acetate to give 4-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (188 mg).

Fuente