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

HRID 1052396Notes

Reaction equation

HRID 1052396 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.O>CN(C)C=O>[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 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 53807105-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidineYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (2 g, 13.02 mmol) was dissolved in 20 mL dimethylformamide. N-Bromosuccinimide (2.55 g, 14.33 mmol) was added under argon atmosphere. The reaction was stirred at room temperature overnight. The crude was poured into water and the precipitate formed was filtered and washed with water. The yellow solid obtained was dried in the vacuum oven to give 2.77 g (91.5% yield) of the title compound. Purity 99%.

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered
  3. washwashed with water
  4. customThe yellow solid obtained
  5. customwas dried in the vacuum oven

Sources & evidence

ORD record
ord-da6ce30c0f8e4445a675c72e4ad85685
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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