Réaction #2146756

Équation de réaction

aluminum

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

N-iodosuccinimide

→

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

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreTo a 250 ml round-bottomed flask, protected
2. 2
   AutreThe solvent is removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue is dissolved in methylene chloride (250 ml)
4. 4
   LavageThe reaction mixture is washed with brine (50 ml)
5. 5
   Autrethe organic layer is separated
6. 6
   Séchagedried over Na2SO4
7. 7
   Concentrationconcentrated in vacuo
8. 8
   AutreThe crude residue is purified by flash-chromatography on silica gel
9. 9
   Lavageeluted with 60% EtOAc in cyclohexane
10. 10
    workup.ADDITIONFractions containing the desired product (TLC)
11. 11
    Autreevaporated

Mode opératoire

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.

Source