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Synthesis of 9‐[(2‐chloro‐6‐fluorophenyl) [ 14 C]methyl]‐9 H ‐purine‐6‐amine (arprinocid) and 9‐[(2,6‐dichlorophenyl) [ 14 C]methyl]‐9 H ‐purine‐6‐amine
Author(s) -
Ellsworth Robert L.,
Meriwether Henry T.,
Mertel Holly E.
Publication year - 1989
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.2580271102
Subject(s) - chemistry , benzoic acid , amine gas treating , reagent , carbon 14 , methylene , medicinal chemistry , purine metabolism , purine , organic chemistry , enzyme , physics , quantum mechanics
The synthesis of 9‐[(2‐chloro‐6‐fluorophenyl)methyl]‐9 H ‐purin‐6‐amine (arprinocid, a coccidiostat candidate) and 9‐[(2,6‐dichlorophenyl)methyl]‐9 H ‐purin‐6‐amine labeled with carbon‐14 in the benzylic methylene carbon of each of these is described. Introduction of the carbon‐14 label leading to the formation of the key radioactive intermediates, 2‐chloro‐6‐fluoro[carboxyl‐ 14 C]benzoic acid and 2,6‐dichloro‐[carboxyl‐ 14 C]benzoic acid, was accomplished by utilizing [ 14 C]carbon dioxide for carbonation of a suitable dihalo‐phenyl Grignard or organolithium reagent.