반응 #2146756

반응 방정식

aluminum

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

N-iodosuccinimide

→

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

용매

DMF

반응 조건

후처리

1. 1
   기타To a 250 ml round-bottomed flask, protected
2. 2
   기타The solvent is removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue is dissolved in methylene chloride (250 ml)
4. 4
   세척The reaction mixture is washed with brine (50 ml)
5. 5
   기타the organic layer is separated
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated in vacuo
8. 8
   기타The crude residue is purified by flash-chromatography on silica gel
9. 9
   세척eluted with 60% EtOAc in cyclohexane
10. 10
    workup.ADDITIONFractions containing the desired product (TLC)
11. 11
    기타evaporated

실험 절차

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.

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