Acetic Acid → HCID 178433420, compound

HRID 2079568Notes

Reaction equation

HRID 2079568 reaction equation
[NH2:1][C:2]1[N:3]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([Br:18])=[CH:13][C:12]=2[CH3:19])[C:4](=[O:10])[CH:5]([CH3:9])[C:6]=1[C:7]#[N:8].[C:20](OC(=O)C)(=O)[CH3:21].C(O)(=[O:29])C>>[Br:18][C:14]1[CH:13]=[C:12]([CH3:19])[C:11]([N:3]2[C:2]3[N:1]=[C:20]([CH3:21])[N:8]=[C:7]([OH:29])[C:6]=3[CH:5]([CH3:9])[C:4]2=[O:10])=[C:16]([CH3:17])[CH:15]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 671036822-amino-1-(4-bromo-2,6-dimethylphenyl)-4-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carbonitrile

Product 1

HCID 178433420HCID 178433420, compound

Procedure

To a suspension of 2-amino-1-(4-bromo-2,6-dimethylphenyl)-4-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carbonitrile (100 g) in acetic acid (100 mL) was added acetic anhydride (38.3 g) and the mixture was heated at reflux for 8 hours. After cooling to room temperature, the solvent was concentrated under reduced pressure, and water was added and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was crystallized from a mixture of ethyl acetate and diisopropylether to give 7-(4-bromo-2,6-dimethylphenyl)-4-hydroxy-2,5-dimethyl-5,7-dihydropyrrolo[2,3-d]pyrimidin-6-one (56.6 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 8 hours
  3. concentrationthe solvent was concentrated under reduced pressure, and water
  4. additionwas added
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe residue was crystallized from a mixture of ethyl acetate and diisopropylether

Sources & evidence

ORD record
ord-8aa5e18ad44a49ee8c29f58ede782e96
Source dataset
uspto-grants-2011_04
Patent number
US07932259B2

Reaction notes

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