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Synthesis of 5-fluoro-3-[3-[4-(2-[14C]-5-methoxy-4-pyrimidinyl)-1piperazinyljpropypiperazinyl]propyl]-1H-indole dihydrochloride

✍ Scribed by Ute J. Haynes; J. E. Swigor

Publisher
John Wiley and Sons
Year
1994
Tongue
French
Weight
209 KB
Volume
34
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The synthesis of 5‐Fluoro‐3‐[3‐[4‐(2‐[^14^C]‐5‐methoxy‐4‐pyrimi‐dinyl)‐1‐piperazinyl]propyl]‐1H‐indole dihydrochloride (5) was achieved by coupling [^14^C] formamidine acetate (1) and dimethylmethoxymalonate in methanol containing sodium methoxide at 60°C to provide 2‐[^14^C] 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‐[^14^C]‐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).

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