Tetrabutylammonium Fluoride → 1-benzyl-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-5-hydroxyiminomethyl-2,4(1H,3H)-pyrimidinedione

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-bromo-3-[4-(2-methoxyphenyl)piperazin-1-yl]propane (1.09 g, 3.5 mmol), prepared as in Example 25, 1-benzyl-5-hydroxyiminomethyl-2,4(1H,3H)-pyrimidinedione (0.86 g, 3.5 mmol), tetrabutylammonium fluoride (4.5 g, 17.5 mmol) and acetonitrile (50 mL) was stirred 24 hours at 25° C. The reaction mixture then was concentrated in vacuo and the residue was dissolved in ethyl acetate (50 mL). The solution was washed with water (3×50 mL) and brine (1×50 mL) and purified by preparative thin, layer chromatography on silica gel eluting with methylene chloride/methanol (95:5) and 1% ammonium hydroxide to give 1-benzyl-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-5-hydroxyiminomethyl-2,4(1H,3H)-pyrimidinedione (250 mg, 0.6mmol). The free base was recrystallized from a solution of fumaric acid in alcohol to give 1-benzyl-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-5-hydroxyiminomethyl-2,4(1H,3H)-pyrimidinedione fumarate, m.p. 198°-200° C.; Anal.: Calcd. for C26H31N5O4.C4H4O4 : C, 59.78; H, 6.02; N, 11.62%; Found: C, 59.74; H, 6.03; N, 11.83%.

Provenance & Evidence