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

HRID 1910868Notes

Reaction equation

HRID 1910868 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.CO>[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

5

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]pyrimidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (E-1) (3.99 g, 26.0 mmol, 1.0 eq) in dry DCM (150 mL) under argon, N-bromosuccinimide (6.02 g, 33.8 mmol, 1.3 eq) is added and the resulting mixture is stirred at RT for 3 h. The reaction mixture is diluted with MeOH (30 mL) and then concentrated in vacuo to yield a slight brown solid. The residue is triturated with H2O (150 mL). The solid is collected by filtration and then re-crystallized in MeOH to afford the product, 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (E-2).

Workup

  1. concentrationconcentrated in vacuo
  2. customto yield a slight brown solid
  3. customThe residue is triturated with H2O (150 mL)
  4. filtrationThe solid is collected by filtration
  5. customre-crystallized in MeOH

Sources & evidence

ORD record
ord-d721edb91b8c47c8afbf1d1a95e6e3d0
Source dataset
uspto-grants-2013_12
Patent number
US08604032B2

Reaction notes

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