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

HRID 2246370Notes

Reaction equation

HRID 2246370 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-908d91a507424decab3bbd1ea907b5f9
Source dataset
uspto-grants-2010_03
Patent number
US07687507B2

Reaction notes

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