تفاعل #2146756

معادلة التفاعل

aluminum

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

N-iodosuccinimide

→

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

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىTo a 250 ml round-bottomed flask, protected
2. 2
   أخرىThe solvent is removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue is dissolved in methylene chloride (250 ml)
4. 4
   غسيلThe reaction mixture is washed with brine (50 ml)
5. 5
   أخرىthe organic layer is separated
6. 6
   تجفيفdried over Na2SO4
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىThe crude residue is purified by flash-chromatography on silica gel
9. 9
   غسيلeluted with 60% EtOAc in cyclohexane
10. 10
    workup.ADDITIONFractions containing the desired product (TLC)
11. 11
    أخرىevaporated

الإجراء التجريبي

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.

المصدر