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Synthesis of 5‐fluoro‐3‐[3‐[4‐(2‐[ 14 C]‐5‐methoxy‐4‐pyrimidinyl)‐1piperazinyljpropypiperazinyl]propyl]‐1H‐indole dihydrochloride
Author(s) -
Haynes Ute J.,
Swigor J. E.
Publication year - 1994
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580340114
Subject(s) - chemistry , sodium methoxide , indole test , methanol , medicinal chemistry , hydrochloric acid , catalysis , organic chemistry , nuclear chemistry
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 ).