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

HRID 473677Notes

Reaction equation

HRID 473677 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 reaction mixture 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 mixture was filtered through celite and concentrated in vacuo to give the title compound. MS (ESI, pos. ion) m/z: 183.1.

Workup

  1. customThe reaction mixture was flushed with argon
  2. customA hydrogen balloon was then attached to the reaction
  3. filtrationthe reaction mixture was filtered through celite and
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf8551b3d76b4c059eab820300919940
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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