N-bromobutanimide → 7-Bromo-1,5-dihydro-4H-pyrrolo[3,2-D]pyrimidin-4-one

HRID 244452Notes

Reaction equation

HRID 244452 reaction equation
[N:1]1[C:6]2[CH:7]=[CH:8][NH:9][C:5]=2[C:4](=[O:10])[NH:3][CH:2]=1.[Br:11]N1C(=O)CCC1=O>CN(C=O)C.O>[Br:11][C:7]1[C:6]2[N:1]=[CH:2][NH:3][C:4](=[O:10])[C:5]=2[NH:9][CH:8]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1354888819-Deazahypoxanthine

Product 1

HCID 1357437117-Bromo-1,5-dihydro-4H-pyrrolo[3,2-D]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one (200 mg, 1.5 mmol, 1 equiv.) and N-bromosuccinimide (320 mg, 1.8 mmol, 1.2 equiv.) in 10 mL of DMF was stirred for 18 hours at room temperature. The reaction was diluted with water and resulting solid was collected by filtration, dried, suspended in MeOH, and filtered. The filtrate was concentrated in vacuo to provide 7-bromo-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one as a beige solid which was used without further purification.

Workup

  1. customresulting solid
  2. filtrationwas collected by filtration
  3. customdried
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a550ae5e2aa142108b291cbe43087a57
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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