反応 #6622

反応方程式

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

収率 65.4%

溶媒

dimethylformamide

反応条件

後処理

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

実験手順

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.

出典