4-[4-(Benzyloxy)butyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one → 4-(4-Hydroxybutyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 1847038Notes

Reaction equation

HRID 1847038 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:18](=[O:19])[CH:17]=[N:16][C:15]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[N:23][C:14]1=2)C1C=CC=CC=1>C(OCC)(=O)C.ClCCl.[O-2].[O-2].[Mn+4]>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:18](=[O:19])[CH:17]=[N:16][C:15]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[N:23][C:14]1=2

Participants

5

Reactant 1

HCID 867249624-[4-(Benzyloxy)butyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

Product 1

HCID 867249634-(4-Hydroxybutyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-oneYield 88%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[4-(benzyloxy)butyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (847 mg, 2.5 mmol) in ethyl acetate (20 ml) 20% palladium hydroxide (400 mg) was added and the catalytic hydrogenation was carried out at room temperature for 90 minutes. After removing the catalyst by filtration, the solvent was removed under reduced pressure, the obtained residue was dissolved in dichloromethane (20 ml) to which manganese dioxide (1.09 g, 12.5 mmol) was then added, and the mixture was stirred overnight at room temperature. After removing manganese dioxide by filtration, the solvent of the filtrate was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 548 mg (88%) of the title compound in the form of a light brown solid.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. customthe solvent was removed under reduced pressure
  4. additionwas then added
  5. customAfter removing manganese dioxide
  6. filtrationby filtration
  7. customthe solvent of the filtrate was removed under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-12c944561158410e850bbc7500abe1e4
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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