Potassium Carbonate → 2-[3-Chloro-2-(1-methylethylsulfonylaminocarbonyl)phenoxy]-4,6dimethoxypyrimidine

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Reaction Steps

A stirred solution of 0.43 grams (0.001 mole) of 4-nitrophenyl 6-chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzoate (prepared in Steps F and G), 0.12 gram (0.001 mole) of 1-methylethylsulfonamide, and 0.14 gram (0.001 mole) of potassium carbonate in 5 mL of acetonitrile was heated at reflux for five hours. The reaction mixture was then cooled and concentrated under reduced pressure to a residue. The residue was stirred with ethyl acetate and water, and the aqueous layer was separated. The aqueous layer was acidified with aqueous dilute hydrochloric acid and then was extracted with ethyl acetate. The extract was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was crystallized from diethyl ether. The solid was collected by filtration to yield 0.16 gram of 2-[3-chloro-2-(1-methylethylsulfonylaminocarbonyl)phenoxy]-4,6dimethoxypyrimidine; m.p. 150°-152° C., Compound 10 in Table 1. The nmr spectrum was consistent with the proposed structure.

Provenance & Evidence