N-bromobutanimide → 7-bromo-6-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidine

HRID 2408474Notes

Reaction equation

HRID 2408474 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:16][C:15]2[CH:14]=[N:13][CH:12]=[N:11][C:10]=2[CH:9]=1.[Br:17]N1C(=O)CCC1=O>CC(C)=O.CCOC(C)=O>[Br:17][C:9]1[C:10]2[N:11]=[CH:12][N:13]=[CH:14][C:15]=2[NH:16][C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 674703356-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 674702947-bromo-6-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidineYield 60%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a slurry of 6-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidine (1.0 g) in acetone (50 mL) was added N-bromosuccinimide (1.0 g). The reaction was stirred at rt for 2 h, until complete conversion was observed by LC-MS. The reaction mixture was diluted with EtOAc (150 mL) and the solid was collected via filtration and washed with EtOAc yielding 820 mg of desired (60% yield). LCMS calculated for C12H7BrFN3 292.1, found 292.23: [M+].

Workup

  1. filtrationthe solid was collected via filtration
  2. washwashed with EtOAc yielding 820 mg

Sources & evidence

ORD record
ord-29caa8f3ac254f088cbeb43a78df9de0
Source dataset
uspto-grants-2014_08
Patent number
US08815858B2

Reaction notes

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