反应 #2393

反应方程式

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

收率 81.3%

溶剂

ammonium chloride

反应条件

后处理

1. 1
   温度cooled to room temperature
2. 2
   萃取extracted with ethyl acetate
3. 3
   洗涤The organic layer is washed with water and brine
4. 4
   干燥dried over sodium sulfate
5. 5
   过滤filtered
6. 6
   浓缩concentrated under reduced pressure
7. 7
   其他The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=40:1)
8. 8
   其他recrystallized from ethyl acetate/n-hexane

实验过程

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.

来源