2-(3,6-dihydro-2H-pyran-4-yl)-3-fluoropyrazine → 2-fluoro-3-(Tetrahydro-2H-pyran-4-yl)pyrazine

HRID 887456Notes

Reaction equation

HRID 887456 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:12]([F:13])=[N:11][CH:10]=[CH:9][N:8]=2)[CH2:3][CH2:2]1>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[F:13][C:12]1[C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[N:8][CH:9]=[CH:10][N:11]=1

Participants

4

Reactant 1

HCID 593511782-(3,6-dihydro-2H-pyran-4-yl)-3-fluoropyrazine

Product 1

HCID 593512282-fluoro-3-(Tetrahydro-2H-pyran-4-yl)pyrazine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottomed flask was added 2-(3,6-dihydro-2H-pyran-4-yl)-3-fluoropyrazine (1.1754 g, 6.52 mmol) and palladium hydroxide on carbon (0.458 g, 0.652 mmol) in EtOAc (21.75 mL). The round bottomed flask was flushed with argon and then placed under vacuum three times. A hydrogen balloon was then attached to the reaction. After stirring overnight, the reaction was filtered through celite to provide 2-fluoro-3-(Tetrahydro-2H-pyran-4-yl)pyrazine. [M+H]=183.1.

Workup

  1. customThe round bottomed flask was flushed with argon
  2. customA hydrogen balloon was then attached to the reaction
  3. filtrationthe reaction was filtered through celite

Sources & evidence

ORD record
ord-48db84fece684ccbb05fcbab8cfa944a
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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