تفاعل #6622

معادلة التفاعل

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

المردود 65.4%

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe solid is collected by filtration, air
2. 2
   أخرىdried
3. 3
   درجة الحرارةrefluxed in 200 mL of methanol
4. 4
   درجة الحرارةThe mixture is cooled
5. 5
   ترشيحthe solid collected by filtration
6. 6
   workup.DISSOLUTIONdissolved in two liters of 10% methanol in methylene chloride
7. 7
   أخرىchromatographed over silica
8. 8
   أخرىInitial black bands are rechromatographed
9. 9
   أخرىthe combined colorless bands from the first and second runs are evaporated

الإجراء التجريبي

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.

المصدر