【作者】 解洪祥； 项金宝； 郑连友； 党群； 柏旭；

【Author】 XIE Hong-xiang,XIANG Jin-bao,ZHENG Lian-you,DANG Qun,BAI Xu~* (The Center for combinatorial Chemistry and Drug Discovery,College of Chemistry and School of Pharmaceutical Sciences,Jilin University,75 Haiwai St.,Changchun,jilin 130012,P.R.china)

【机构】 吉林大学组合化学与创新药物研究中心、化学院和药学院；

【摘要】 目的研究"叔胺效应"在5-胺基取代的-6,7-二氢-5H-吡咯并[2,3-d]嘧啶衍生物合成中的应用。方法以4,6-二氯-5-醛基嘧啶为原料,经两步取代反应得到关键前体原料2-[（5-醛基-6-苯巯基嘧啶-4-基）（甲基）氨基]乙酸甲酯（3）,然后与多种一级胺在二甲苯回流的条件下反应制得5-胺基取代的-6,7-二氢-5H-吡咯[2,3-d]嘧啶衍生物。结果以38%-85%产率得到单一cis构型产物,结构均经质谱（MS）、核磁氢谱（¹H-NMR）和核磁碳谱(¹³C-NMR)确证。结论该热环合反应操作简单,不用任何催化剂即可单一的生成cis构型的5-胺基取代的-6,7-二氢-5H-吡咯并[2,3-d]嘧啶化合物,具有一定的适用性。这一方法在其它四氢吡咯并环化合物合成中的应用正在研究中。更多还原

【Abstract】 OBJECTIVE To investigate the application of the tert-amino effect in the synthesis of variously substituted 5-amino-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine derivatives.METHODS The key precursor methyl 2-（（5-formyl-6-（phenylthio）pyrimidin-4-yl）（methyl）amino）acetate（3）,prepared from 4,6-dichloro-5-formylpyrimidine（1） in two-step nucleophilic substitution reactions,reacted with various amines under refluxing xylene to provide the 5-amino-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine derivatives.RESULTS The cis-configured products were prepared in 38%-85%yield.The structures were characterized by MS,¹H-NMR and ¹³C-NMR.CONCLUSION The cis-configured 5 -amino-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine derivatives could be synthesized,by using a simple operating in absence of any catalyst.Application of this strategy in other pyrrolidine fused compounds will be investigated in the near future.更多还原