N-Iodosuccinimide → 2,4-Dichloro-5-iodo-7H-pyrrolo(2,3-d)pyrimidine

HRID 2381605Notes

Reaction equation

HRID 2381605 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[I:12]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[C:10]([I:12])=[CH:9][NH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 574159022,4-Dichloro-5-iodo-7H-pyrrolo(2,3-d)pyrimidineYield 55.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (3.00 g, 16.0 mmol) in CH2Cl2 (30 mL), N-iodosuccinimide (3.60 g, 16.0 mmol) was added. It was stirred at room temperature for 20 h. The fine precipitate was collected, dried on vacuum to give 2,4-dichloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (2.80 g). MS 314.1 and 316.1 (M+H)

Workup

  1. additionwas added
  2. customThe fine precipitate was collected
  3. customdried on vacuum

Sources & evidence

ORD record
ord-aa8e0bed0f0346479dc0e0c8a0e3016c
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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