反応 #2146756

反応方程式

aluminum

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

N-iodosuccinimide

→

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

溶媒

DMF

反応条件

後処理

1. 1
   その他To a 250 ml round-bottomed flask, protected
2. 2
   その他The solvent is removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue is dissolved in methylene chloride (250 ml)
4. 4
   洗浄The reaction mixture is washed with brine (50 ml)
5. 5
   その他the organic layer is separated
6. 6
   乾燥dried over Na2SO4
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The crude residue is purified by flash-chromatography on silica gel
9. 9
   洗浄eluted with 60% EtOAc in cyclohexane
10. 10
    workup.ADDITIONFractions containing the desired product (TLC)
11. 11
    その他evaporated

実験手順

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.

出典