Dimethyl Sulfoxide → 2-[4-(4-Methoxycarbonylbenzoyl)benzyloxy]-3-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1291359Notes

Reaction equation

HRID 1291359 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[N:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]2=[N:4][C:3]1=[O:13].[CH3:14][O:15][C:16]([C:18]1[CH:33]=[CH:32][C:21]([C:22]([C:24]2[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=2)=[O:23])=[CH:20][CH:19]=1)=[O:17].CS(C)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:14][O:15][C:16]([C:18]1[CH:33]=[CH:32][C:21]([C:22]([C:24]2[CH:25]=[CH:26][C:27]([CH2:28][O:13][C:3]3[N:4]=[C:5]4[CH:12]=[CH:11][CH:10]=[CH:9][N:6]4[C:7](=[O:8])[C:2]=3[CH3:1])=[CH:30][CH:31]=2)=[O:23])=[CH:20][CH:19]=1)=[O:17]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 51632663-Methylpyrido[1,2-a]pyrimidine-2,4-dioneHCID 212180324-(4-Methoxycarbonylbenzoyl)benzyl bromide

Product 1

HCID 189193412-[4-(4-Methoxycarbonylbenzoyl)benzyloxy]-3-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methylpyrido[1,2-a]pyrimidine-2,4-dione (2.20 g, 12.5 mmol) and 4-(4-methoxycarbonylbenzoyl)benzyl bromide (7.04 g, 12.7 mmol) in DMF (40.0 ml)-DMSO (20.0 ml) was added potassium carbonate (3.92 g, 28.4 mmol) and the mixture was stirred at room temperature overnight. This reaction mixture was diluted with water and the resulting crystals were collected by filtration, dissolved in ethyl acetate, and dried over MgSO4. The solvent was then distilled off under reduced pressure and the residue was re-crystallized from ethyl acetate to provide colorless needles.

Workup

  1. filtrationthe resulting crystals were collected by filtration
  2. dissolutiondissolved in ethyl acetate
  3. dry with materialdried over MgSO4
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customthe residue was re-crystallized from ethyl acetate
  6. customto provide colorless needles

Sources & evidence

ORD record
ord-c8ec30e8a046440f94ade46fc2101c5f
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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