Synthesis of 1-(2′-deoxy-2′-fluoro-β-D-arabinofuranosyl)-[Methyl-11C]thymine ([11C]FMAU) via a Stille cross-coupling reaction with [11C]methyl iodide

被引:38
|
作者
Samuelsson, L
Långström, B
机构
[1] Uppsala Univ, Inst Chem, Dept Organ Chem, SE-75121 Uppsala, Sweden
[2] UAS, Uppsala Res Imaging Solut AB, SE-75185 Uppsala, Sweden
来源
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS | 2003年 / 46卷 / 03期
关键词
1-(2 '-deoxy-2 '-fluoro-beta-D-arabinofuranosyl)-[methyl-C-11-] thymine; C-11]-FMAU; Stille coupling; C-11]methyl iodide; palladium;
D O I
10.1002/jlcr.668
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)-[methyl-C-11]thymine ([C-11]FMAU) [C-11]-(1) under bar was synthesised via a palladium-mediated Stille coupling reaction of 1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)-5-(trimethylstannyl)uracil (2) under bar with [C-11]methyl iodide in a one-pot procedure. The reaction conditions were optimized by screening various catalysts and solvents, and by altering concentrations and reaction temperatures. The highest yield was obtained using Pd-2(dba)(3) and P(o-tolyl)(3) in DMF at 130degreesC for 5 min. Under these conditions the title compound [C-11]-(1) under bar was obtained in 28 +/- 5% decay-corrected radiochemical yield calculated from [C-11]methyl iodide (number of experiments=7). The radiochemical purity was >99% and the specific radioactivity was 0.1GBq/mumol at 25 min after end of bombardment. In a typical experiment 700-800 MBq of [C-11]FMAU [C-11]-(1) under bar was obtained starting from 6-7 GBq of [C-11]methyl iodide. A mixed C-11/C-13 synthesis to yield [C-11]-(1) under bar/(C-13)-(1) under bar followed by C-13-NMR analysis was used to confirm the labelling position. The labelling procedure was found to be suitable for automation. Copyright (C) 2002 John Wiley Sons, Ltd.
引用
收藏
页码:263 / 272
页数:10
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