Acetic Acid → HCID 178433420, compound

HRID 1253829Notes

Reaction equation

HRID 1253829 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-dbcb38824ce74e8a92f1ec5c1b87a96b
Source dataset
uspto-grants-2013_06
Patent number
US08455511B2

Reaction notes

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