Acetic Acid → HCID 178433420, compound

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

Reactant 3

HCID 176Acetic Acid

HCID 7918Acetic Anhydride

HCID 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).