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]=1Participants
4
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.
Workup
- customafterwards the solvent was removed under reduced pressure
- dissolutionThe residue was dissolved several times in toluene
- customthe solvent removed under reduced pressure
- dissolutionThe resulting solid was dissolved in 1,2-dichloroethane-MeOH (1:1)
- additionacetaldehyde and sodium cyanoborohydride were added
- stirringthe mixture stirred at room temperature
- customAfter 30 minutes the solvent was removed under reduced pressure
- washthe residue washed with H2O
Sources & evidence
- ORD record
- ord-7ec9e274c3ae4fa8837c6beb51aac66a
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07939537B2
Reaction notes
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