[H-].[Na+].[NH2:3]/[C:4](/[C:11]([F:14])([F:13])[F:12])=[CH:5]\[C:6]([O:8]CC)=O.[Cl:15][C:16]1[C:21]2[O:22][C:23]([CH3:26])([CH3:25])[O:24][C:20]=2[C:19]([N:27]=[C:28]=[O:29])=[C:18]([F:30])[CH:17]=1.[C:31](=O)([O-])[O-].[K+].[K+].CI>O.O1CCCC1>[Cl:15][C:16]1[C:21]2[O:22][C:23]([CH3:26])([CH3:25])[O:24][C:20]=2[C:19]([N:27]2[C:6](=[O:8])[CH:5]=[C:4]([C:11]([F:12])([F:13])[F:14])[N:3]([CH3:31])[C:28]2=[O:29])=[C:18]([F:30])[CH:17]=1A mixture of 0,32 g (0.0079 mole) of sodium hydride and 200 mL of dry tetrahydrofuran was cooled to -20 ° C, and 1.26 g (0.0069 mole) of ethyl 3-amino-4,4,4-trifluorocrotonate was added in a dropwise manner. This mixture was stirred for 10 minutes, and then 1.68 g (0.0069 mole) of 7-chloro-2,2-dimethyl-5-fluoro-1,3-benzodioxol-4-yl isocyanate was added in a dropwise manner. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature at which it was stirred for one hour. At the conclusion of this period the reaction mixture was heated to 85 ° C. at which it was stirred for approximately 16 hours. Then 0.95 g (0.0069 mole) of potassium carbonate and 1.96 g (0.0138 mole) of methyl iodide were added to the reaction mixture, and it was heated at 75 ° C for seven hours. At the conclusion of this period, water was added to the reaction mixture, and the resulting mixture was extracted with diethyl ether. The extracts were washed with water, dried over anhydrous magnesium sulfate, filtered, and the solvent evaporated from the filtrate under reduced pressure, leaving a residue. This residue was passed through a column of silica gel, eluting with ethyl acetate:heptane (4:1). Product-containing fractions were combined, and the solvent was evaporated under reduced pressure, leaving 0.58 g of 3-(7-chloro-2,2-dimethyl-5-fluoro- 1,3-benzodioxol-4-yl)-1 -methyl-6-trifluoromethyluracil (Compound 5) as an oil. The NMR spectrum was consistent with the proposed structure.
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