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

HRID 2191997Notes

Reaction equation

HRID 2191997 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-9e7bc0a9d8f84f36af09f2e114371f5f
Source dataset
uspto-grants-2012_12
Patent number
US08329700B2

Reaction notes

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