Methanol → 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
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.CO>CN(C=O)C>[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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (4-1) (1.53 g, 10.0 mmol) in DMF (20 mL) was added N-bromosuccinimide (1.78 g, 10.0 mmol) in DMF (10 mL) dropwise at 0° C. The reaction mixture was stirred at 0° C. for 30 min and then at room temperature for 1 h. Methanol (25 mL) was added, and the reaction mixture was stirred for an additional 1 h. The solvent was evaporated and the residue was crystallized from methanol to give the title compound as white solid.
Workup
- waitat room temperature for 1 h
- stirringthe reaction mixture was stirred for an additional 1 h
- customThe solvent was evaporated
- customthe residue was crystallized from methanol
Sources & evidence
- ORD record
- ord-ee0bb1355c2d4cecbe8f82f074459bf3
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07323453B2
Reaction notes
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