Réaction #6622

Équation de réaction

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

Rendement 65.4%

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   FiltrationThe solid is collected by filtration, air
2. 2
   Autredried
3. 3
   Températurerefluxed in 200 mL of methanol
4. 4
   TempératureThe mixture is cooled
5. 5
   Filtrationthe solid collected by filtration
6. 6
   workup.DISSOLUTIONdissolved in two liters of 10% methanol in methylene chloride
7. 7
   Autrechromatographed over silica
8. 8
   AutreInitial black bands are rechromatographed
9. 9
   Autrethe combined colorless bands from the first and second runs are evaporated

Mode opératoire

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.

Source