HCID 57998845, compound → HCID 57998831, compound

HRID 1093915Notes

Reaction equation

HRID 1093915 reaction equation
C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cl:13][C:14]1[CH:15]=[C:16]([Pb+3])[CH:17]=[CH:18][C:19]=1[Cl:20].[OH:22][C:23]1[C:32]2[C:27](=[N:28][CH:29]=[CH:30][N:31]=2)[NH:26][C:25](=[O:33])[CH:24]=1>CN(C)C1C=CN=CC=1.CS(C)=O.C(OCC)(=O)C>[Cl:13][C:14]1[CH:15]=[C:16]([C:24]2[C:25](=[O:33])[NH:26][C:27]3=[N:28][CH:29]=[CH:30][N:31]=[C:32]3[C:23]=2[OH:22])[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

6

Reactant 2

HCID 57998845HCID 57998845, compoundHCID 178476545HCID 178476545, compound

Product 1

HCID 57998831HCID 57998831, compoundYield 27.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3,4-dichlorophenyl lead triacetate (1.63 g), 8-hydroxy-5H-pyrido[2,3-b]pyrazin-6-one (0.254 g) and 4-dimethylaminopyridine (DMAP) (0.549 g) in anhydrous dimethylsulfoxide (10 mL) under a nitrogen atmosphere was heated to 60° C. for four hours. The reaction mixture was then allowed to cool to ambient temperature and stored at ambient temperature for 16 hours. The reaction mixture was diluted with ethyl acetate. The mixture was washed with aqueous hydrochloric acid (1M) and water, and the organic layer concentrated to give 7-(3,4-dichlorophenyl)-8-hydroxy-5H-pyrido[2,3-b]pyrazin-6-one (0.13 g) which was used without further purification.

Workup

  1. temperatureto cool to ambient temperature
  2. washThe mixture was washed with aqueous hydrochloric acid (1M) and water
  3. concentrationthe organic layer concentrated

Sources & evidence

ORD record
ord-5673cfd98060475f86e65a3df3657e09
Source dataset
uspto-grants-2012_03
Patent number
US08133847B2

Reaction notes

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