7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro- → 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

HRID 2246372Notes

Reaction equation

HRID 2246372 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]NC(=O)CCC(N)=O>C(Cl)(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 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 9834204N-Bromosuccinamide

Product 1

HCID 53807105-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidineYield 89%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (30 g/0.02 mol) dissolved in 75 mL of chloroform was added 3.5 g (0.02 mol) of N-bromosuccinamide and the resulting mixture refluxed for 1 h. After cooling to room temperature, the precipitate was removed by filtration and dried under reduced pressure affording 4.1 g (89%) of the title compound. 1H NMR (400 MHz) (CDCl3) δ: 7.93 (d, 1H, J=2.8 Hz), 8.60 (s, 1H).

Workup

  1. temperaturethe resulting mixture refluxed for 1 h
  2. customthe precipitate was removed by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-842b0ad0b6ad4ee5b2b8cb8d54505f10
Source dataset
uspto-grants-2010_03
Patent number
US07687507B2

Reaction notes

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