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

HRID 423069Notes

Reaction equation

HRID 423069 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:11]2[CH:18]=[CH:17][NH:16][C:12]=2[N:13]=[CH:14][N:15]=1>C(Cl)Cl>[Br:1][C:18]1[C:11]2[C:10]([Cl:9])=[N:15][CH:14]=[N:13][C:12]=2[NH:16][CH:17]=1

Participants

4

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 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

N-Bromosuccinimide (6.84 g, 38.42 mmol) was added portionwise to 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (5 g, 32.56 mmol) in DCM, dry (125 mL) at 20° C. under nitrogen. The resulting suspension was stirred at 20° C. for 1 hour. The reaction mixture was evaporated and the resulting brown solid was triturated with water to give a purple solid which was collected by filtration. The crude solid was triturated with hot MeOH to give a solid which was collected by filtration. The hot trituration was repeated to give 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (5.23 g, 69.1%) as a cream solid.

Workup

  1. customdry (125 mL) at 20° C. under nitrogen
  2. customThe reaction mixture was evaporated
  3. customthe resulting brown solid was triturated with water
  4. customto give a purple solid which
  5. filtrationwas collected by filtration
  6. customThe crude solid was triturated with hot MeOH
  7. customto give a solid which
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-955965977bb44357904e4bcc27386b6b
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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