N-Iodosuccinimide → 4-Chloro-5-iodo-2-methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 1750286Notes

Reaction equation

HRID 1750286 reaction equation
[Cl:1][C:2]1[C:3]2[CH:11]=[CH:10][NH:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[I:12]N1C(=O)CCC1=O>ClCCl>[Cl:1][C:2]1[C:3]2[C:11]([I:12])=[CH:10][NH:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 109208984-CHLORO-2-METHYL-7H-PYRROLO[2,3-D]PYRIMIDINE

Product 1

HCID 665707094-Chloro-5-iodo-2-methyl-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-2-methyl-7H-pyrrolo[2,3-d]pyrimidine (400 mg, 2.4 mmol) in dichloromethane (10 mL) was added N-iodosuccinimide (537 mg, 2.39 mmol). The mixture was stirred at room temperature for 2 hours, then washed with aqueous sodium sulfite solution, dried over sodium sulfate, filtered, and concentrated in vacuo to provide the product as a brown solid. Yield: 330 mg, 1.12 mmol, 47%. LCMS m/z 293.8[M+H+].

Workup

  1. washwashed with aqueous sodium sulfite solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74f17f59bafd4ada96f0342e0110db1f
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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