Methyl iodide → HCID 70300048, compound

Participants

Reaction Steps

A solution of 3-[4-chloro-6-fluoro-3-methyl-1,2(2H)-benzisoxazol-7-yl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (3.5 g, 0.010 mole), methyl iodide (2.1 g, 0.014 mole), potassium carbonate (2.0 g, 0.003 mole), and THF (100 mL) was heated to reflux where it stirred for five hours. The reaction mixture was then cooled to ambient temperature where it stirred for about 72 hours. After this time, the reaction mixture was poured into water and thoroughly extracted with ether. The combined extracts were washed with water and an aqueous saturated sodium chloride solution. The organic layer was separated, dried with magnesium sulfate, and concentrated to a residue. The residue was subjected to silica gel column chromatography using 9:1 to 5:1 hexane and ethyl acetate. The product-containing fractions provided 2.0 grams of Compound 27, m.p. 218-219° C. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence