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J Nucl Med. 2008; 49 (Supplement 1):46P
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Radiopharmaceutical Chemistry: New Chemistry-Other

Novel Radiolabeling Approaches

Click chemistry – One step synthesis of [18F/19F] 5-(l-(2-fluoroethyl)-lH-l,2,3-triazol-4-yl)-l-((2R, 4S, 5R )-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4-(lH, 3H)-dione

Uwe Ackermann1, Henri Tochon-Danguy1, John Sachinidis1, Stan Poniger1 and Andrew Scott2

1 Centre for PET and Nuclear Medicine, Austin Health, Heidelberg, Victoria, Australia; ; 2 Ludwig Institute for Cancer Research, Melbourne, Victoria, Australia

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Objectives: The previously reported synthesis of [18F/19F] 5-(l-(2-fluoroethyl)-lH-l,2,3-triazol-4-yl)-l-((2R, 4S, 5R )-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4-(lH, 3H)-dione (1) involves multiple synthesis steps, starting from 5-ethynyl-2’-deoxyuridine (2). Our aim was to develop a one step click chemistry synthesis method for [18F/19F] 1 starting from [18F/19F] fluoroethylazide and 2.

Methods: Radiochemistry [18F] Fluoroethylazide was prepared from toluenesulfonic acid-2-azidoethyl ester and distilled into a reaction vessel. To this vessel was added 2 in DMF with a buffered solution of CuSO4 and L-ascorbic acid. The vessel was heated to 80°C for 20 min and the reaction mixture purified by reversed phase HPLC, giving [18F] 1 in 70% radiochemical yield. The HPLC retention time of [18F] 1 was identical to [19F] 1. Cold chemistry [19F] Fluoroethylazide, prepared from 2-Fluoroethyl tosylate and NaN3 in anhydrous DMF, was added to a solution of 2, CuSO4 and L-ascorbic acid. The reaction was stirred at 80°C for 4h and purified by flash chromatography to give [19F] 1. NMR shifts matched the published values.

Results: We have been able to establish the synthesis and use of [18F/19F] fluoroethylazide for the click chemistry preparation of [18F/19F] 1. This method produces the target compound in a single synthesis step starting from unprotected EDU and is a significant improvement on the previously reported synthesis protocol.

Conclusions: Using [18F/19F] fluoroethylazide can be a convenient way for the one step click chemistry preparation of radiopharmaceuticals as well as their cold standards.

Research Support: Supported by the AHMRF





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