ethyl 4-(4-bromophenyl)-6-methyl-2-(piperidin-1-yl)pyrimidine-5-carboxylate | 1245716-63-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl 4-(4-bromophenyl)-6-methyl-2-(piperidin-1-yl)pyrimidine-5-carboxylate
• 英文别名: Ethyl 4-(4-bromophenyl)-6-methyl-2-piperidin-1-ylpyrimidine-5-carboxylate
• CAS: 1245716-63-5
• 化学式: C₁₉H₂₂BrN₃O₂
• 分子量: 404.307
• InChiKey: XKNUDRDOBBBJIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Ethyl 4-(4-bromophenyl)-1,2-dihydro-6-methyl-2-oxopyrimidin-5-carboxylate 在 三乙胺 作用下， 以 四氯化碳 为溶剂， 反应 1.33h， 生成 ethyl 4-(4-bromophenyl)-6-methyl-2-(piperidin-1-yl)pyrimidine-5-carboxylate
  参考文献：
  名称：

  嘧啶-2-基磷酸酯的亲核取代反应，使用胺和硫醇作为PEG-400介导的亲核性环保溶剂

  摘要：

  摘要 已经开发了通过嘧啶-2-基磷酸与胺和苯硫酚在PEG-400中的反应来无金属合成C2官能化的嘧啶。在不使用任何催化剂或其他添加剂的情况下，可以在环境友好的PEG-400中以理想的产率产生所需的产物。 已经开发了通过嘧啶-2-基磷酸与胺和苯硫酚在PEG-400中的反应来无金属合成C2官能化的嘧啶。在不使用任何催化剂或其他添加剂的情况下，可以在环境友好的PEG-400中以理想的产率产生所需的产物。

  DOI：

  10.1055/s-0035-1560175

文献信息

• Copper(<scp>i</scp>) chloride promoted Csp²–N cross-coupling of 1,2-di(pyrimidin-2-yl) disulfides with amines: an efficient approach to obtain C2-amino functionalized pyrimidines
  作者：Kai-Jie Wei、Zheng-jun Quan、Zhang Zhang、Yu-xia Da、Xi-cun Wang

  DOI：10.1039/c5ob02535d

  日期：——

  The copper(I)-promoted cross-coupling of 1,2-di(pyrimidin-2-yl) disulfides with aromatic amines and aliphatic amines to deliver C–N coupling products in moderate to good yields is reported in this paper. Central to this strategy is the conversion of disulfides into aryl- and alkyl amines by a copper-promoted chemoselective C–S bond cleavage.

  本文报道了铜（Ⅰ）促进的1，2-二（嘧啶-2-基）二硫化物与芳族胺和脂族胺的交叉偶联，以中等至良好的产率提供了C-N偶联产物。该策略的核心是通过铜促进的化学选择性C–S键裂解将二硫化物转化为芳基和烷基胺。
• Synthesis of 2-Substituted Pyrimidines via Cross-Coupling Reaction of Pyrimidin-2-yl Sulfonates with Nucleophiles in Polyethylene Glycol 400
  作者：Xi-Cun Wang、Guo-Jun Yang、Zheng-Jun Quan、Peng-Yan Ji、Jun-Ling Liang、Rong-Guo Ren

  DOI：10.1055/s-0030-1258080

  日期：2010.7

  A mild and rapid procedure to the synthesis of 2-substituted pyrimidines was developed via sequential functionalization of easily available Biginelli 3,4-dihydropyrimidine-2(1H)-ones via oxidation, esterification, followed by cross-coupling reaction of pyrimidin-2-yl sulfonates with N, S, and O nucleophiles in PEG-400 as a green reaction medium at room temperature.

  通过氧化、酯化以及嘧啶-2-的交叉偶联反应对容易获得的 Biginelli 3,4-二氢嘧啶-2(1H)-酮进行顺序功能化，开发了一种温和且快速的合成 2-取代嘧啶的方法在室温下作为绿色反应介质，在 PEG-400 中使用 N、S 和 O 亲核试剂制备基磺酸盐。
• Synthesis of C2-functionalized pyrimidines from 3,4-dihydropyrimidin-2(1H)-ones by the Mitsunobu coupling reaction
  作者：Xi-Cun Wang、Guo-Jun Yang、Xiao-Dong Jia、Zhang Zhang、Yu-Xia Da、Zheng-Jun Quan

  DOI：10.1016/j.tet.2011.02.046

  日期：2011.5

  The Biginelli 3,4-dihydropyrimidin-2(1H)-one was converted to various C2-multifunctionalized pyrimidines via the dehydrogenation and Mitsunobu reaction using amines, alcohols, phenols and carboxylic acids as nucleophiles. A possible mechanism was also proposed to rationalize the formation of products.

  通过使用胺，醇，酚和羧酸作为亲核试剂的脱氢和Mitsunobu反应，将Biginelli 3,4-dihydropyrimidin-2（1 H）-one转化为各种C 2-多官能嘧啶。还提出了一种可能的机制来合理化产品的形成。
• Molecular iodine-mediated S–N and C–N cross-coupling and oxidative aromatization of 3,4-dihydropyrimidin-2(1H)-thiones with secondary amines
  作者：Zheng-Jun Quan、Ying Lv、Zhong-Jie Wang、Zhang Zhang、Yu-Xia Da、Xi-Cun Wang

  DOI：10.1016/j.tetlet.2013.01.113

  日期：2013.4

  A domino S-N and C-N coupling/oxidative aromatization process to synthesize 2-aminothio-phenylpyrimidines and 2-amino-phenylpyrimidines by S-N and C-N cross-coupling reactions is described. This methodology couples 3,4-dihydropyrimidine-2-thiones and secondary amines catalyzed by molecular iodine. Remarkably the C-N coupled product was obtained via a desulfitative coupling-aromatization reaction in one-pot reaction. (C) 2013 Elsevier Ltd. All rights reserved.