Reacción #2388

Ecuación de reacción

potassium fluoride

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

2-thienyltributyltin

dioxane

→

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

Rendimiento 69.3%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturais refluxed for 80 minutes
2. 2
   TemperaturaAfter cooling
3. 3
   Lavadothe reaction solution is washed
4. 4
   Otrodried
5. 5
   Otroevaporated
6. 6
   Otroto remove the solvent
7. 7
   OtroThe residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=30:1~10:1)
8. 8
   Otrocrystallized from methylene chloride/n-hexane

Procedimiento

A mixture of 4-tert-butyl-N-[6-{2-(5-bromopyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)-2-n-propylpyrimidin-4-yl]benzenesulfonamide (300 mg), 2-thienyltributyltin (670 mg), bis(triphenylphosphine)palladium (II) chloride (16 mg) and dioxane (5 ml) is refluxed for 80 minutes. After cooling, the reaction solution is diluted with ethyl acetate, and thereto is added 10% aqueous potassium fluoride solution. The mixture is stirred at room temperature for one hour, and the reaction solution is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=30:1~10:1), and crystallized from methylene chloride/n-hexane to give 4-tert-butyl-N-[6-{2-(5-(2-thienyl)pyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)-2-n-propylpyrimidin-4-yl]-benzenesulfonamide (209 mg) as crystals.

Fuente