Triethylamine → 6-Fluoro-3-[(2-methyl-3-oxo-1-cyclopenten-1-yl)oxy]-2pyrazinecarbonitrile

HRID 392370Notes

Reaction equation

HRID 392370 reaction equation
Cl[C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5](Cl)=[CH:6][N:7]=1.[F-:11].[K+].[CH3:13][CH:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20].C(N(CC)CC)C>CS(C)=O.O.C(OCC)(=O)C>[F:11][C:5]1[N:4]=[C:3]([C:9]#[N:10])[C:2]([O:19][C:18]2[CH2:17][CH2:16][C:15](=[O:20])[C:14]=2[CH3:13])=[N:7][CH:6]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 130052-Methyl-1,3-cyclopentanedioneHCID 522689Potassium FluorideHCID 226628453,6-Dichloropyrazine-2-carbonitrile

Product 1

HCID 226628306-Fluoro-3-[(2-methyl-3-oxo-1-cyclopenten-1-yl)oxy]-2pyrazinecarbonitrileYield 42.3%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

In 60 mL of dimethyl sulfoxide was dissolved 3.0 g of 3,6-dichloro-2-pyrazinecarbonitrile. After adding 3.0 g of potassium fluoride, the mixture thus obtained was stirred at 90-100° C. for 2 hours. The reaction mixture was returned to room temperature, to which were successively added 2.1 g of 2-methyl-1,3-cyclopentandione and 7.2 ml of triethylamine. The mixture thus obtained was stirred at room temperature for one hour. The reaction mixture was added to a mixture of 50 mL of ethyl acetate and 200 mL of water, and the organic layer was separated. The organic layer thus obtained was washed successively with water and saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=2:1] to obtain 1.7 g of 6-fluoro-3-[(2-methyl-3-oxo-1-cyclopenten-1-yl)oxy]-2pyrazinecarbonitrile as a yellow-colored solid product.

Workup

  1. customthe mixture thus obtained
  2. customwas returned to room temperature, to which
  3. customThe mixture thus obtained
  4. stirringwas stirred at room temperature for one hour
  5. customthe organic layer was separated
  6. customThe organic layer thus obtained
  7. washwas washed successively with water and saturated aqueous solution of sodium chloride
  8. dry with materialdried on anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=2:1]

Sources & evidence

ORD record
ord-784edebb176347d0ab6c64e54abfb226
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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