Potassium Fluoride → HCID 22662803, compound
Reaction equation
Br[C:2]1[N:3]=[C:4]([C:16]#[N:17])[C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.[F-:18].[K+]>CS(C)=O>[C:16]([C:4]1[C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=[C:2]([F:18])[N:3]=1)#[N:17]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
In 10.5 mL of dimethyl sulfoxide was dissolved 0.35 g of t-butyl 5-bromo-3-cyano-2-pyrazinylcarbamate. After adding 0.17 g of potassium fluoride, the mixture was stirred first at 70° C. for 30 minutes and then at 90° C. for 30 minutes to form t-butyl 3-cyano-5-fluoro-2-pyrazinylcarbamate in the reaction system. Then, 0.17 g of potassium fluoride was added and stirred at 90° C. for 40 minutes. The reaction mixture was returned to room temperature and added to a mixture of 30 ml of ethyl acetate and 60 mL of water, pH was adjusted to 8 with saturated aqueous solution of sodium hydrogen carbonate, and the organic layer was separated. The organic layer thus obtained was washed with saturated aqueous solution of sodium chloride and dried on anhydrous sodium 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=3:1] to obtain 20 mg of 3-amino-6-fluoro-2-pyrazinecarbonitrile as a yellow-colored solid product.
Sources & evidence
- ORD record
- ord-cc6613561daf4791b3d49a6cbf55e692
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06800629B2
Reaction notes
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