Reacción #2393

Ecuación de reacción

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

trimethylsilylacetylene

triethylamine

dimethylformamide

→

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

Rendimiento 81.3%

Disolventes

ammonium chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   LavadoThe organic layer is washed with water and brine
4. 4
   Secadodried over sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=40:1)
8. 8
   Otrorecrystallized from ethyl acetate/n-hexane

Procedimiento

A mixture of 4-tert-butyl-N-{6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (1.00 g), trimethylsilylacetylene (330 mg), bis(triphenylphosphine)palladium (II) chloride (58 mg), copper (I) iodide (32 mg), triethylamine (420 mg) and dimethylformamide (5 ml) is stirred at 50° C. for three hours under argon atmosphere, and cooled to room temperature. The mixture is diluted with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer is washed with water and brine, and dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=40:1), and recrystallized from ethyl acetate/n-hexane to give 4-tert-butyl-N-{6-[2-(5-trimethylsilylethynylpyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (837 mg) as colorless crystalline powder.

Fuente