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Synthesis of 5‐trifluoromethyluracil‐2− 14 C
Author(s) -
Zambito Arthur J.,
Chamberlin Earl M.
Publication year - 1971
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590070415
Subject(s) - chloroacetic acid , thiourea , chemistry , sulfur , yield (engineering) , hydrogen fluoride , flue gas desulfurization , medicinal chemistry , hydrogen , uracil , organic chemistry , nuclear chemistry , materials science , metallurgy , dna , biochemistry
Diethyl ethoxymethylenemalonate was condensed with thiourea− 14 C in the presence of sodium ethylate to give ethyl 2‐thio‐6‐oxypyrimidine‐5‐carboxylate‐2− 14 C. Desulfurization of the latter pyrimidine with chloroacetic acid gave uracil‐5‐carboxylic acid‐2− 14 C, which was subsequently fluorinated with sulfur tetrafluoride and hydrogen fluoride to afford the desired 5‐trifluoromethyluracil‐2− 14 C in 25.6% overall yield based on thiourea.