Reaktion #6624

Reaktionsgleichung

3-(3-tetrahydropyr-2-yloxyprop-1-yn-1-yl)-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine

methanol

quinoline

hydrogen

→

3-(3-tetrahydropyr-2-yloxyprop-1-en-1-yl)-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine

Lösungsmittel

chloroform

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent then is removed by evaporation
2. 2
   workup.ADDITIONthe residue diluted with methylene chloride
3. 3
   FiltrationThe methylene chloride solution is filtered through silica gel with 2% methanol in methylene chloride
4. 4
   Sonstigeto remove catalyst
5. 5
   Einengenthe filtrate then concentrated
6. 6
   Sonstigeto give an oil which

Vorschrift

A mixture of 2 g of 3-(3-tetrahydropyr-2-yloxyprop-1-yn-1-yl)-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine, 40 ml of methanol, 20 ml of chloroform, 40 mg of 5% palladium on barium sulfate, and 40 mg of synthetic quinoline is stirred under 1 atmosphere hydrogen pressure for 40 min. The solvent then is removed by evaporation and the residue diluted with methylene chloride. The methylene chloride solution is filtered through silica gel with 2% methanol in methylene chloride to remove catalyst and the filtrate then concentrated to give an oil which upon adding ether yields 3-(3-tetrahydropyr-2-yloxyprop-1-en-1-yl)-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine which can be further purified through column chromatography eluting with ethyl acetate and recrystallization using ethyl acetate.

Quelle