N-bromobutanimide → 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

HRID 1937398Notes

Reaction equation

HRID 1937398 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.[Br:11]N1C(=O)CCC1=O>C(Cl)Cl>[Br:11][C:10]1[C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=2[NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 53807105-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidineYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.21 g, 1.4 mmol) in dry methylene chloride (10 ml) was added N-bromosuccinimide (0.26 g, 1.5 mmol) at ambient temperature. The reaction mixture was stirred for 18 hours, and the resulting solid filtered with methylene chloride washes and dried in vacuo to afford 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine as a tan powder (0.28 g, 88%). GC-MS: 233 (MH+), RT: 4.42 min.

Workup

  1. filtrationthe resulting solid filtered with methylene chloride washes
  2. customdried in vacuo

Sources & evidence

ORD record
ord-8b98b22d2f1c4149a88ca69fae227ae7
Source dataset
uspto-grants-2002_05
Patent number
US06395733B1

Reaction notes

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