Allyl bromide → 1-Methyl-3-(1-allyl-2-oxo-6-fluoro-1,2-dihydroquinoline-7-yl)-6-(trifluoromethyl)-pyrimidine-2,4(1H,3H)-dione

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Reaction Steps

These compounds were prepared in a manner analogous to that of Step I of Example 1, using 0.5 gram (0.001 mole) of 3-(6-fluoroquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracil (prepared in Step H of Example 1), 0.5 gram (0.003 mole) of 3-bromopropene, and 0.4 gram (0.003 mole) potassium carbonate in 40 mL of N,N-dimethylformamide. The crude reaction product was subjected to column chromatography on silica gel. Elution was accomplished using 1:1 ethyl acetate-heptane and ethyl acetate. The appropriate, product-containing fractions were combined and concentrated under reduced pressure, yielding 0.3 gram of 3-[1-(2-propen-1-yl)-6-fluoroquinolin-2-on-7-yl]-1-methyl-6-trifluoromethyluracil (Compound 26), mp 178°-179° C. Other product-containing fractions were combined and concentrated under reduced pressure, yielding 0.2 gram of the O-alkylated product, 3-[2-(2-propen-1-yloxy)-6-fluoroquinolin-2-on-7-yl]-1-methyl-6-trifluoromethyluracil (Compound 20A). The NMR spectra were consistent with the proposed structures.

Provenance & Evidence