N-Iodosuccinimide → HCID 178447244, compound

HRID 1510921Notes

Reaction equation

HRID 1510921 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[NH:5][C:4]2=[N:15][CH:16]=[CH:17][C:3]=12.[I:18]N1C(=O)CCC1=O>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:11])[CH3:12])[NH:5][C:4]2=[N:15][CH:16]=[C:17]([I:18])[C:3]=12

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178447243HCID 178447243, compound

Product 1

HCID 178447244HCID 178447244, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-2-trimethylacetamido-pyrrolo[2,3-d]pyrimidine (9a, 10.9 g, 43.24 mmol) was dissolved in anhydrous THF (120 mL) under nitrogen. After the addition of N-iodosuccinimide (10.7 g, 47.56 mmol), the mixture was stirred at RT for 1 h. The solvent was then removed in vacuo. The residue dissolved in EtOAc (100 mL) and washed with 1 M sodium thiosulfate (3×100 mL). Column chromatography purification (2% MeOH in DCM, isocratic) yielded 9b (12.9 g).

Workup

  1. customThe solvent was then removed in vacuo
  2. dissolutionThe residue dissolved in EtOAc (100 mL)
  3. washwashed with 1 M sodium thiosulfate (3×100 mL)
  4. customColumn chromatography purification (2% MeOH in DCM, isocratic)

Sources & evidence

ORD record
ord-163d365933ab4db29d548a7573a926bc
Source dataset
uspto-grants-2012_07
Patent number
US08212020B2

Reaction notes

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