1,2-Bis(4-methylphenyl)-1,2-ethanedione → 7-Chloro-2,3-dip-tolylpyrido[2,3-b]pyrazine

HRID 517925Notes

Reaction equation

HRID 517925 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[C:10]1([CH3:27])[CH:15]=[CH:14][C:13]([C:16](=O)[C:17]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=O)=[CH:12][CH:11]=1>CCO>[Cl:1][C:2]1[CH:7]=[N:6][C:5]2=[N:8][C:16]([C:13]3[CH:12]=[CH:11][C:10]([CH3:27])=[CH:15][CH:14]=3)=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[N:9]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 769961,2-Bis(4-methylphenyl)-1,2-ethanedioneHCID 12682545-Chloropyridine-2,3-diamine

Product 1

HCID 666663497-Chloro-2,3-dip-tolylpyrido[2,3-b]pyrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising 5-chloropyridine-2,3-diamine (1 g, 6.9 mmol) and 1,2-di-p-tolylethane-1,2-dione (1.6 g, 6.9 mmol) in EtOH (15 ml) under argon was stirred at 70° C. overnight. The mixture was heated for a further 8 hours and the solvent was removed under reduced pressure. The resulting crude material was purified by chromatography on silica eluting with 5% EtOAc in hexane to afford the titled compound;

Workup

  1. temperatureThe mixture was heated for a further 8 hours
  2. customthe solvent was removed under reduced pressure
  3. customThe resulting crude material was purified by chromatography on silica eluting with 5% EtOAc in hexane

Sources & evidence

ORD record
ord-b45ca3cd30674dd3b6c33af08b7a920b
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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