Reacción #2146756

Ecuación de reacción

aluminum

4-chloro-7H-pyrrolo[2,3-d]pyrimidine

N-iodosuccinimide

→

4-chloro-5-iodo-pyrrolo[2,3-d]pyrimidine

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo a 250 ml round-bottomed flask, protected
2. 2
   OtroThe solvent is removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue is dissolved in methylene chloride (250 ml)
4. 4
   LavadoThe reaction mixture is washed with brine (50 ml)
5. 5
   Otrothe organic layer is separated
6. 6
   Secadodried over Na2SO4
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   OtroThe crude residue is purified by flash-chromatography on silica gel
9. 9
   Lavadoeluted with 60% EtOAc in cyclohexane
10. 10
    workup.ADDITIONFractions containing the desired product (TLC)
11. 11
    Otroevaporated

Procedimiento

To a 250 ml round-bottomed flask, protected from light with aluminum foil, are added 4-chloro-7H-pyrrolo[2,3-d]pyrimidine 1 (2.15 g, 14.0 mmol) and N-iodosuccinimide (3.37 g, 14.98 mmol) dissolved in anhydrous DMF. The reaction mixture is stirred at room temperature under nitrogen for 16 hrs. The solvent is removed in vacuo, and the residue is dissolved in methylene chloride (250 ml). The reaction mixture is washed with brine (50 ml), and the organic layer is separated, dried over Na2SO4, and concentrated in vacuo. The crude residue is purified by flash-chromatography on silica gel and eluted with 60% EtOAc in cyclohexane. Fractions containing the desired product (TLC) are pooled and evaporated to afford 4-chloro-5-iodo-pyrrolo[2,3-d]pyrimidine as a pale-yellow solid.

Fuente