Hydrogen iodide → 4-iodo-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine

HRID 400558Notes

Reaction equation

HRID 400558 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1.[IH:21]>O>[I:21][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 442289674-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 586917404-iodo-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidineYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[5 g. 16.2 mmol] of 4-Chloro-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine was added in small portions, to 100 mL of cold stirring 47% stabilized hydriodic acid at 0° C. and stirred for one hour cold; the temperature was then allowed to warm to ambient temperature and stirred an additional 5 hrs. The reaction mixture was diluted with water and the solid was isolated via suction filtration, the solid being washed with additional water. The crude solid was dissolved in dichloromethane and washed twice with saturated sodium hydrogen carbonate solution, brined, dried (Na2SO4) and the solvent was removed under reduced pressure and triturated with a 2:1 mixture of hexanes/MTBE to yield 5.7 g of a white material (88%).

Workup

  1. customat 0° C.
  2. stirringstirred for one hour cold
  3. stirringstirred an additional 5 hrs
  4. customthe solid was isolated via suction filtration
  5. washthe solid being washed with additional water
  6. dissolutionThe crude solid was dissolved in dichloromethane
  7. washwashed twice with saturated sodium hydrogen carbonate solution
  8. dry with materialdried (Na2SO4)
  9. customthe solvent was removed under reduced pressure
  10. customtriturated with a 2:1 mixture of hexanes/MTBE

Sources & evidence

ORD record
ord-4379acf8ba5a423a9073083c85c76d3b
Source dataset
uspto-grants-2014_06
Patent number
US08741912B2

Reaction notes

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