Academic Journal
Palladium-mediated oxidative carbonylation reactions for the synthesis of 11C-radiolabelled ureas.
| Title: | Palladium-mediated oxidative carbonylation reactions for the synthesis of 11C-radiolabelled ureas. |
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| Authors: | Kealey, Steven1,2, Husbands, Stephen M.3, Bennacef, Idriss4, Gee, Antony D.5, Passchier, Jan2 |
| Source: | Journal of Labelled Compounds & Radiopharmaceuticals. Apr2014, Vol. 57 Issue 4, p202-208. 7p. |
| Subject Terms: | *Urease genetics, *Carbonylation, *Radiolabeling, *Radioactive tracers, *Positron emission tomography, *Aliphatic amines |
| Abstract: | Palladium(II)-mediated oxidative carbonylation reactions have been used to synthesize 11C-radiolabelled ureas via the coupling of amines with [11C]carbon monoxide, in a one-pot process. Following trapping of 11CO in a solution of copper(I) tris(3,5-dimethylpyrazolyl)borate, homocoupling reactions of primary aliphatic amines proceed in the presence of Pd(PPh3)2Cl2 to give the corresponding N, N-disubstituted [11C]ureas. Secondary amines do not produce the corresponding N, N, N, N-tetrasubsituted [11C]ureas under these conditions. This difference in reactivity allows for the formation of unsymmetrical N, N', N'-trisubstituted [11C]ureas using a mixture of a primary amine and a reactive secondary amine. The potential use of this method in positron emission tomography (PET) was demonstrated by the synthesis of the M1 muscarinic acetylcholine receptor radiotracer, [11C- carbonyl]GSK1034702. [ABSTRACT FROM AUTHOR] |
| Database: | Academic Search Index |
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