反应 #6622

反应方程式

3-iodo-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine

dimethyl N-(4-ethynylbenzoyl)-L-glutamate

triethylamine

water

→

dimethyl N-[4-(4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidin-3-ylethynyl)benzoyl]-L-glutamate

收率 65.4%

溶剂

dimethylformamide

反应条件

后处理

1. 1
   过滤The solid is collected by filtration, air
2. 2
   其他dried
3. 3
   温度refluxed in 200 mL of methanol
4. 4
   温度The mixture is cooled
5. 5
   过滤the solid collected by filtration
6. 6
   workup.DISSOLUTIONdissolved in two liters of 10% methanol in methylene chloride
7. 7
   其他chromatographed over silica
8. 8
   其他Initial black bands are rechromatographed
9. 9
   其他the combined colorless bands from the first and second runs are evaporated

实验过程

To a mixture of 3.6 g (10 mmol) of well-dried 3-iodo-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine in 40 mL of dimethylformamide are added 4.0 g (13.19 mmol) of dimethyl N-(4-ethynylbenzoyl)-L-glutamate, 0.38 g of copper (I) iodide, 3 mL of triethylamine, and 1.0 g of tetrakis-(triphenylphosphine)palladium. This mixture is stirred at ambient temperatures for two hours and then poured into 500 mL of water. The solid is collected by filtration, air dried, and then refluxed in 200 mL of methanol. The mixture is cooled and the solid collected by filtration, dissolved in two liters of 10% methanol in methylene chloride, and chromatographed over silica. Initial black bands are rechromatographed and the combined colorless bands from the first and second runs are evaporated to give 3.5 g of dimethyl N-[4-(4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidin-3-ylethynyl)benzoyl]-L-glutamate which can be purified further by recrystallization from 50% methanol in methylene chloride.

来源