Water → 3-[4-(Benzyloxy)phenoxy]-6-fluoro-2-pyrazinecarbonitrile

HRID 392366Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][C:14]2[C:15]([C:21]#[N:22])=[N:16][C:17](Cl)=[CH:18][N:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-:25].[K+].C(OCC)(=O)C.O>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][C:14]2[C:15]([C:21]#[N:22])=[N:16][C:17]([F:25])=[CH:18][N:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 105 °C

Procedure

In 70 ml of dimethyl sulfoxide was dissolved 3.50 g of 3-[4-(benzyloxy)phenoxy]-6-chloro-2-pyrazinecarbonitrile. After adding 3.01 g of potassium fluoride, the mixture was stirred at 100-110° C. for 3 hours. The reaction mixture was returned to room temperature and added to a mixture of 70 mL of ethyl acetate and 350 mL of water, and the organic layer was separated. The organic layer thus obtained was washed with 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: toluene:ethyl acetate=5:1] to obtain 1.88 g of 3-[4-(benzyloxy)phenoxy]-6-fluoro-2-pyrazinecarbonitrile as a white-colored solid product.

Workup

customwas returned to room temperature
customthe organic layer was separated
customThe organic layer thus obtained
washwas washed with saturated aqueous solution of sodium chloride
dry with materialdried on anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe residue thus obtained
customwas purified by silica gel column chromatography [eluent: toluene:ethyl acetate=5:1]

Sources & evidence

ORD record: ord-dce0e30d812d4c8691137c57ac1a8d50
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800629B2

Reaction notes

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