新型5-溴嘧啶衍生物的选择性合成  

Selective Synthesis of Novel 5-Bromopyrimidine Derivatives

作　　者：张扬[1] 吴洋[1] 张灯青[1] 金武松[1] 

机构地区：[1]东华大学化学化工与生物工程学院,上海201620

出　　处：《合成化学》2011年第5期662-664,共3页Chinese Journal of Synthetic Chemistry

摘　　要：对甲苯磺酰氯与三甘醇单甲酯完成酯化反应,再与对溴苯酚缩合制得对溴苯基三甘醇单甲醚(3);3与硼酸甲酯完成取代反应、酸解后在Pd(PPh3)4催化下与5-溴-2-碘嘧啶(5)在甲苯中通过Suzuki偶联反应选择性地合成了5-溴-2-对(甲基三甘醇基)苯基嘧啶(1a),收率73%。以1-十二烯和5为主要原料,通过Suzuki偶联反应,一锅法选择性地合成了5-溴-2-十二烷基嘧啶(1b),收率82%。1a和1b未见文献报道,其结构经1HNMR,13C NMR和MS表征。p-Bromophenyl-methoxy triethylene glycol（3） was prepared by esterification of p- tolylsulfonyl chloride with methoxy triethylene glycol, then condensation with p-bromophenol. Novel 5-bromo-2- [ p- （ methyl triethylene glycol group） phenyl ] pyrimidine （ 1 a） in yield of 73 % was selectively synthesized using Pd（ PPh3 ）4 as a catalyst in toluene under Ar gas by Suzuki-coupling of 5-bromo-2- iodopyrimidine （ 5 ） and p-（ methyl triethylene glycol group） phenyl-borie acid （4） which was obtained by substitution reaction of 3 with methyl borate, then acidolysis. Novel 5-bromo-2-dodecylpyrimidine （lb） in yield of 82% was selectively synthesized by Suzuki-coupling in ＂one-pot＂ from 1-dodecylene and 5 using Pd（dppf） Cl2 as a catalyst in THF. The structures of la and lb were characterized by 1H NMR, 13C NMR and MS.

关 键 词：5-溴嘧啶 SUZUKI偶联反应 一锅法 合成 

分 类 号：O625.6[理学—有机化学]