Sodium Bicarbonate → 7-Ethyl-2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

HRID 517927Notes

Reaction equation

HRID 517927 reaction equation
[CH2:1]([C:3]1[CH:26]=[N:25][C:6]2=[N:7][C:8]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=[C:5]2[CH:4]=1)[CH3:2].C([O-])(O)=O.[Na+]>CCO.[Pd]>[CH2:1]([CH:3]1[CH2:26][NH:25][C:6]2=[N:7][C:8]([C:18]3[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=[C:5]2[CH2:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 89690245HCID 89690245, compound

Product 1

HCID 896898537-Ethyl-2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-Ethyl-2,3-di-p-tolylpyrido[2,3-b]pyrazine (2 g, 5.89 mmol) in EtOH (5 ml) was treated with Pd/C (0.2 g) and placed under an atmosphere of hydrogen. After stirring overnight the mixture was treated with a catalytic quantity of NaHCO3 and stirring continued under hydrogen overnight. The mixture was passed through Celite® (filter material) and the solvent was removed under reduced pressure. Purification of the crude product by chromatography on silica eluting with 5% EtOAc in hexane afforded the titled compound;

Workup

  1. stirringstirring
  2. waitcontinued under hydrogen overnight
  3. filtrationThe mixture was passed through Celite® (filter material)
  4. customthe solvent was removed under reduced pressure
  5. customPurification of the crude product by chromatography on silica eluting with 5% EtOAc in hexane

Sources & evidence

ORD record
ord-39c1ccf1825f4236beca890ecbd9b5c7
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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