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

HRID 1892132Notes

Reaction equation

HRID 1892132 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]NC(=O)C.O>C(Cl)Cl>[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 4353N-BromoacetamideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 53807105-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidineYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1.2 g, 7.8 mmol) in CH2Cl2 (25 ml) was added N-bromoacetamide (1.186 g, 8.6 mmol) in CH2Cl2 (25 ml). The mixture was heated at reflux temperature for 40 mins, then cooled to room temperature, and concentrated under vacuum to give an off-white solid. Cold water (40 ml) was added to the solid, which was then collected by filtration, washed with cold water (5 ml), and dried under vacuum. The product was recrystallized from a minimum amount of isopropanol to yield pure 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1.475 g, 81.5%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 40 mins
  3. concentrationconcentrated under vacuum
  4. customto give an off-white solid
  5. filtrationwas then collected by filtration
  6. washwashed with cold water (5 ml)
  7. customdried under vacuum
  8. customThe product was recrystallized from a minimum amount of isopropanol

Sources & evidence

ORD record
ord-68fde106b46f4fb5b7c41dbf1efa01ea
Source dataset
uspto-grants-2013_08
Patent number
US08507672B2

Reaction notes

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