Reacción #6626

Ecuación de reacción

3-iodo-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine

trimethylsilylacetylene

triphenylphosphine

triethylamine

→

3-trimethylsilylethynyl-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 3 hours
2. 2
   OtroThe solvent is removed under reduced pressure
3. 3
   Otrothe residue triturated with 1:1 ethyl acetate
4. 4
   Filtraciónhexanes and filtered
5. 5
   OtroThe solid thus collected
6. 6
   workup.DISSOLUTIONis dissolved in methylene chloride
7. 7
   ConcentraciónThe eluate is concentrated

Procedimiento

A mixture of 2.0 g of 3-iodo-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine, 1.2 g. of trimethylsilylacetylene, 0.1 g of palladium chloride, 0.23 g of triphenylphosphine, 0.06 g of cuprous iodide, and 2.6 g of triethylamine in 100 mL of acetonitrile is heated in a sealed tube for 1.5 hours at 50° C. and then at reflux for 3 hours. The solvent is removed under reduced pressure and the residue triturated with 1:1 ethyl acetate:hexanes and filtered. The solid thus collected is dissolved in methylene chloride and this solution is passed through a pad of silica gel eluting with 1% methanol on methylene chloride. The eluate is concentrated to yield 3-trimethylsilylethynyl-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine.

Fuente