Water → 6-Fluoro-3-(4-methoxyphenoxy)-2-pyrazinecarbonitrile

HRID 392365Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:4][CH:3]=1.[F-:19].[K+].C(OCC)(=O)C.O>CS(C)=O>[F:19][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:4][CH:3]=1

Participants

Conditions

Temperature: 105 °C

Procedure

In 39 mL of dimethyl sulfoxide was dissolved 1.95 g of 6-chloro-3-(4-methoxyphenoxy)-2-pyrazinecarbonitrile. After adding 2.16 g of potassium fluoride, the mixture thus obtained was stirred at 100-110° C. for 3 hours. The reaction mixture was returned to room temperature, a mixture of 40 mL of ethyl acetate and 200 mL of water was added, 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: n-hexane:ethyl acetate=5:1] to obtain 1.45 g of 6-fluoro-3-(4-methoxyphenoxy)-2-pyrazinecarbonitrile as a yellow-colored solid product.

Workup

customthe mixture thus obtained
customwas returned to room temperature
additionwas added
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: n-hexane:ethyl acetate=5:1]

Sources & evidence

ORD record: ord-3ec523f84f4545a9b2d2b207876a96c9
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800629B2

Reaction notes

Loading…