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

HRID 869479Notes

Reaction equation

HRID 869479 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]pyrimidineYield 66.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (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) was added and the resulting mixture was stirred at RT for 3 h. The reaction mixture was diluted with MeOH (30 mL) and then concentrated in vacuo to yield a slight brown solid. The residue was triturated with H2O (150 mL). The solid was collected by filtration and then re-crystallized in MeOH to afford 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (4.0 g, 66% yield).

Workup

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

Sources & evidence

ORD record
ord-950369a095c14a6fab49899f1ed90f2d
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

Loading…