U. Haynes, J. E. Swigor
1994
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Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
The synthesis of 5-Fluoro-3-[3-[4-(2-[14C]-5-methoxy-4-pyrimi-dinyl)-1-piperazinyl]propyl]-1H-indole dihydrochloride (5) was achieved by coupling [14C] formamidine acetate (1) and dimethylmethoxymalonate in methanol containing sodium methoxide at 60°C to provide 2-[14C] 4,6-dihydroxy-5-methoxyprimidine (2). Reaction of (2) with phosphorous oxychloride produced the unstable chloro-compound (3) which was reacted with 5-Fluoro-3-(3-N-piperazinylpropyl) indole to give 5-Fluoro-3[3-[4-(2-[14C]-6-chloro-5-methoxy-4-pyrimidinyl)-1-piperazinyl] propyl]-1H-indole (4). Catalytic reduction of (4) and addition of 2 equivalents of hydrochloric acid resulted in the title compound as the dihydrochloride (5).