N-bromobutanimide → 5-Bromo-4-chloro-7-methyl-7H-pyrrolo(2,3-d)pyrimidine

HRID 1909917Notes

Reaction equation

HRID 1909917 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([CH3:11])[C:4]=2[N:5]=[CH:6][N:7]=1.C1C(=O)N([Br:19])C(=O)C1>ClCCl>[Br:19][C:10]1[C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=2[N:8]([CH3:11])[CH:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2658294-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 665451605-Bromo-4-chloro-7-methyl-7H-pyrrolo(2,3-d)pyrimidineYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (12.15 g, 72.5 mmol) in Dichloromethane (DCM) (200 mL) was added NBS (13.55 g, 76 mmol) portionwise, and the reaction mixture was stirred overnight at room temperature. The solvent was evaporated, and the solid was washed with water and dried to afford 5-bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (17 g) as an off-white solid.

Workup

  1. customThe solvent was evaporated
  2. washthe solid was washed with water
  3. customdried

Sources & evidence

ORD record
ord-92316150a0524002954de3a3b1b347a4
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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