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J Labelled Comp Radiopharm. 2014 Apr;57(4):202-8. doi: 10.1002/jlcr.3151. Epub 2013 Dec 11.

Palladium-mediated oxidative carbonylation reactions for the synthesis of (11) C-radiolabelled ureas.

Author information

1
Institute of Psychiatry, De Crespigny Park, King's College London, London, SE5 8AF, UK; Imanova Ltd., Hammersmith Hospital, Du Cane Road, London, W12 0NN, UK.

Abstract

Palladium(II)-mediated oxidative carbonylation reactions have been used to synthesize (11) C-radiolabelled ureas via the coupling of amines with [(11) C]carbon monoxide, in a one-pot process. Following trapping of (11) CO in a solution of copper(I) tris(3,5-dimethylpyrazolyl)borate, homocoupling reactions of primary aliphatic amines proceed in the presence of Pd(PPh3 )2 Cl2 to give the corresponding N,N-disubstituted [(11) C]ureas. Secondary amines do not produce the corresponding N,N,N,N-tetrasubsituted [(11) C]ureas under these conditions. This difference in reactivity allows for the formation of unsymmetrical N,N',N'-trisubstituted [(11) C]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, [(11) C-carbonyl]GSK1034702.

KEYWORDS:

PET; carbon monoxide; carbon-11; carbonylation; palladium; ureas

PMID:
24327390
DOI:
10.1002/jlcr.3151
[Indexed for MEDLINE]
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