Phenyl 5-ethylpyrido[3,4-b]pyrazine-6(5H)-carboxylate → Phenyl 5-ethyl-7,8-dihydropyrido[3,4-b]pyrazine-6(5H)-carboxylate

HRID 132866Notes

Reaction equation

HRID 132866 reaction equation
[CH2:1]([CH:3]1[C:8]2=[N:9][CH:10]=[CH:11][N:12]=[C:7]2[CH:6]=[CH:5][N:4]1[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])[CH3:2]>[Pd].C(OCC)(=O)C>[CH2:1]([CH:3]1[C:8]2=[N:9][CH:10]=[CH:11][N:12]=[C:7]2[CH2:6][CH2:5][N:4]1[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])[CH3:2]

Participants

4

Reactant 1

HCID 69182531Phenyl 5-ethylpyrido[3,4-b]pyrazine-6(5H)-carboxylate

Product 1

HCID 69182558Phenyl 5-ethyl-7,8-dihydropyrido[3,4-b]pyrazine-6(5H)-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Catalyst (10% palladium on carbon, 140 mg) was added to a solution of phenyl 5-ethylpyrido[3,4-b]pyrazine-6(5H)-carboxylate (238 mg, 0.85 mmol) in ethyl acetate (6.0 mL), and the resultant mixture was stirred under hydrogen (1 atm) for 7.5 h. Filtration through Celite® and evaporation of the solvent gave the crude product. Purification by flash chromatography (silica gel, 6-15% ethyl acetate/dichloromethane) gave the title compound as a colorless oil. LC/MS 284 (M+1).

Workup

  1. filtrationFiltration
  2. customthrough Celite® and evaporation of the solvent
  3. customgave the crude product
  4. customPurification by flash chromatography (silica gel, 6-15% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-a8aa9193fad54422b7ce321b64f1c6e7
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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