Chlorosuccinimide → 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidine

HRID 988826Notes

Reaction equation

HRID 988826 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:11]N1C(=O)CCC1=O>ClCCl>[Cl:1][C:2]1[C:3]2[C:10]([Cl:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 111060924,5-dichloro-7H-pyrrolo[2,3-d]pyrimidineYield 72.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (154 mg, 1.0 mmol) was suspended in 6.0 mL of dry dichloromethane in a flame-dried flask and to this mixture was added N-chlorosuccinimide (147 mg, 1.1 mmol) in one portion. The resulting mixture stirred at room temperature for 18 h, at which time the solvent was removed under reduced pressure. The residue was triturated with water and isolated by filtration to afford 137 mg (72%) of the title compound as a gray solid, mp 224-227° C.(dec). LRMS: 188 (M+1).

Workup

  1. customwas removed under reduced pressure
  2. customThe residue was triturated with water
  3. customisolated by filtration

Sources & evidence

ORD record
ord-51fb01c5a26e47bd9d26396dd1ac4323
Source dataset
uspto-grants-2003_10
Patent number
US06635762B1

Reaction notes

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