Propargyl bromide → 1-Methyl-3-[1-(2-propynyl)-2-oxo-6-fluoro-1,2-dihydroquinoline-7-yl]-6-(trifluoromethyl)-pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Steps

A stirred solution of 0.6 gram (0.002 mole) of 3-(6-fluoroquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracil, 0.5 gram (0.003 mole) of 3-bromopropyne, and 0.5 gram (0.003 mole) of potassium carbonate in 40 mL of N,N-dimethylformamide was stirred at ambient temperature for about 16 hours. The reaction mixture was then subjected to column chromatography on silica gel. Elution was accomplished using 1:1 ethyl acetate-heptane and ethyl acetate. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.4 gram of 3-[1-(2-propyn-1-yl)-6-fluoroquinolin-2-on-7-yl]-1-methyl-6-trifluoromethyluracil, mp 236°-238° C. The NMR spectrum was consistent with the proposed structure. Other fractions were combined and concentrated under reduced pressure, yielding a small amount of the O-alkylated product, 3-[2-(2-propyn-1-yloxy)-6-fluoroquinolin-2-on-7-yl]-1-methyl-6-trifluoromethyluracil.

Provenance & Evidence