Acetic Acid → 9-(ethylamino)-N-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-pyrido[1,2-a]pyrimidine-2-carboxamide

Reaction equation

[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[C:21]([NH:22][C:23](=O)OCC4C=CC=CC=4)=[CH:20][CH:19]=[CH:18][N:13]3[C:14](=[O:17])[C:15]=2[OH:16])=[O:9])=[CH:4][CH:3]=1.Br.[C:36](O)(=O)C>>[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[C:21]([NH:22][CH2:23][CH3:36])=[CH:20][CH:19]=[CH:18][N:13]3[C:14](=[O:17])[C:15]=2[OH:16])=[O:9])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 176Acetic Acid

HCID 260Hydrogen Bromide

HCID 86761308Benzyl (2-{[(4-fluorobenzyl)amino]carbonyl}-3-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-yl)carbamate

Product 1

HCID 547306319-(ethylamino)-N-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-pyrido[1,2-a]pyrimidine-2-carboxamide

Procedure

To a solution of benzyl (2-{[(4-fluorobenzyl)amino]carbonyl}-3-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-yl)carbamate in acetic acid was added HBr (30% in AcOH). The solution was stirred at room temperature for 2 hours and afterwards the solvent was removed under reduced pressure. The residue was dissolved several times in toluene and the solvent removed under reduced pressure. The resulting solid was dissolved in 1,2-dichloroethane-MeOH (1:1), acetaldehyde and sodium cyanoborohydride were added, and the mixture stirred at room temperature. After 30 minutes the solvent was removed under reduced pressure and the residue washed with H2O.