반응 #6622

반응 방정식

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

수율 65.4%

용매

dimethylformamide

반응 조건

후처리

1. 1
   여과The solid is collected by filtration, air
2. 2
   기타dried
3. 3
   온도refluxed in 200 mL of methanol
4. 4
   온도The mixture is cooled
5. 5
   여과the solid collected by filtration
6. 6
   workup.DISSOLUTIONdissolved in two liters of 10% methanol in methylene chloride
7. 7
   기타chromatographed over silica
8. 8
   기타Initial black bands are rechromatographed
9. 9
   기타the combined colorless bands from the first and second runs are evaporated

실험 절차

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.

출처