Process for producing fluoroalkoxyaminopyrimidines
AssigneeCiba-Geigy Corporation
InventorRudolf W. Pfluger
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AssigneeCiba-Geigy Corporation
InventorRudolf W. Pfluger
Estimating the term…
A novel process for producing fluoroalkoxyaminopyrimidines of the formula I ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or benzyl, X is halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylamino or di-C.sub.1 -C.sub.4 -alkylamino, and T is hydrogen, chlorofluoromethyl, bromofluoromethyl, difluoromethyl or 1,2,2,2-tetrafluoroethyl, characterized in that a thiopyrimidine of the formula II ##STR2## wherein Y has the meaning given for X under the formula I or is hydroxyl, A is hydrogen, sodium, potassium or an equivalent of calcium or magnesium, and Q is C.sub.1 -C.sub.4 -alkyl, phenyl or benzyl, is reacted with difluorochloromethane, difluorobromomethane, tetrafluoroethylene, perfluoropropylene, trifluorobromoethylene or trifluorochloroethylene in the presence of a base; the resulting compound of the formula III ##STR3## is converted by oxidation into a compound of the formula IV ##STR4## wherein n is the number one or two; and this compound is treated with an amine of the formula V H--NH--R (V).
A process for producing a fluoroalkoxyaminopyrimidine of the formula I ##STR12## wherein R is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or benzyl, X is halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylamino or di-C.sub.1 -C.sub.4 -alkylamino, and T is hydrogen, chlorofluoromethyl, bromofluoromethyl, difluoromethyl or 1,2,2,2-tetrafluoroethyl, characterised in that a thiopyrimidine of the formula II ##STR13## wherein Y has the meaning given for X under the formula I or is hydroxyl, Q is C.sub.1 -C.sub.4 -alkyl, phenyl or benzyl, and A is hydrogen, sodium, potassium or an equivalent of calcium or magnesium, is reacted with difluoromethane, difluorobromomethane, tetrafluoroethylene, perfluoropropylene, trifluorobromoethylene or trifluorochloroethylene in the presence of an inorganic base;
A process for producing a compound of the formula I, characterised in that a thiopyrimidine of the formula II is reacted in dioxane in the presence of an aqueous sodium hydroxide solution, at a temperature of between 20.degree. and 100.degree. C., with difluorochloromethane, difluorobromomethane, tetrafluoroethylene, perfluoropropylene, trifluorobromoethylene or trifluorochloroethylene, the resulting compound of the formula III is converted in methylene chloride with m-chloroperoxybenzoic acid, or in a glacial acetic acid/methylene chloride mixture with potassium permanganate, at a temperature of between -20.degree. and +25.degree. C., or in glacial acetic acid with aqueous hydrogen peroxide solution at a temperature of between 70.degree. and 90.degree. C., by oxidation into a compound of the formula IV, and this compound is treated at a temperature of between 20.degree. and 100.degree. C., under a pressure of between 1 bar and 20 bar, in a methylene chloride/water mixture with an amine of the formula V.
Dependencies are inferred from the claim text.