ethyl 2-(butylamino)-4-methyl-6-phenylpyrimidine-5-carboxylate | 1310479-76-5

• 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 2-(butylamino)-4-methyl-6-phenylpyrimidine-5-carboxylate
• 英文别名: Ethyl 2-(butylamino)-4-methyl-6-phenyl-pyrimidine-5-carboxylate
• CAS: 1310479-76-5
• 化学式: C₁₈H₂₃N₃O₂
• 分子量: 313.4
• InChiKey: QRBKRBUNYJTVKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 在 盐酸 、 噻吩-2-甲酸亚铜(I) 、 lanthanide(III)chloride heptahydrate 、 三(邻甲基苯基)磷 、 palladium dichloride 、 lithium hexamethyldisilazane 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 23.0h， 生成 ethyl 2-(butylamino)-4-methyl-6-phenylpyrimidine-5-carboxylate
  参考文献：
  名称：

  从3,4-二氢嘧啶-1 H -2-硫酮一步合成2-芳基（烷基）氨基嘧啶的脱氢硫C-N交叉偶联和伴随的氧化脱氢

  摘要：

  一种在Pd / Cu催化体系下通过脱硫C–N交叉偶联和伴随的氧化脱氢从容易获得的3,4-二氢嘧啶-1 H -2-硫酮（DHPM）合成2-芳基（烷基）氨基嘧啶的方法描述。该反应方案只需一步即可从多种DHPM和胺偶联伙伴中提供前所未有的完全取代的2-芳基（烷基）氨基嘧啶多样性。

  DOI：

  10.1021/acs.orglett.6b02617

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。
• Nucleophilic Substitution Reaction of Pyrimidin-2-yl Phosphates Using Amines and Thiols as Nucleophiles Mediated by PEG-400 as an Environmentally Friendly Solvent
  作者：Zheng-Jun Quan、Xi-Cun Wang、Ting Xing、Kai-Jie Wei

  DOI：10.1055/s-0035-1560175

  日期：——

  reaction of pyrimidin-2-yl phosphates with amines and thiophenols in PEG-400 has been developed. The desired products can be generated in good to excellent yields in the environmentally friendly PEG-400, without any catalysts or other additives. A metal-free synthesis of C2-functionalized pyrimidines via the reaction of pyrimidin-2-yl phosphates with amines and thiophenols in PEG-400 has been developed

  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。
• Cu-Catalyzed Direct Amination of Cyclic Amides via C–OH Bond Activation Using DMF
  作者：Peng Chen、Kaixiu Luo、Xianglin Yu、Xu Yuan、Xiaoyu Liu、Jun Lin、Yi Jin

  DOI：10.1021/acs.orglett.0c02320

  日期：2020.8.21

  aromatic heterocyclic amines from cyclic amides. The most-reported methods for cyclic amide conversions to aromatic heterocyclic amines use an activating group, such as a halogen atom or a trifluoromethane sulfonyl group. However, subsequent elimination of activating groups during the amination process results in significant waste. This copper-catalyzed direct amination of cyclic amides in DMF forms aromatic

  在这里，我们描述了一种铜催化的方法，可以直接从环状酰胺中获得芳香族杂环胺。用于环酰胺转化为芳族杂环胺的最报道的方法使用活化基团，例如卤素原子或三氟甲烷磺酰基。但是，在胺化过程中随后消除活化基团导致大量浪费。铜催化的DMF中环状酰胺的直接胺化反应形成具有环境友好性且易于获得的试剂的芳香族杂环胺。已经提出该反应的可能的自由基机理。同时，N1原子的配位作用是该反应成功的关键，它为铜离子的C-O键活化和胺化提供了帮助。
• Facile transformation of Biginelli pyrimidin-2(1H)-ones to pyrimidines. In vitro evaluation as inhibitors of Mycobacterium tuberculosis and modulators of cytostatic activity
  作者：Kamaljit Singh、Kawaljit Singh、Baojie Wan、Scott Franzblau、Kelly Chibale、Jan Balzarini

  DOI：10.1016/j.ejmech.2011.03.010

  日期：2011.6

  A series of pyrimidine derivatives bearing amine substituents at C-2 position were obtained from Biginelli 3,4-dihydropyrimidin-2(1H)-ones and the effect of structural variation on anti-TB activity against Mycobacterium tuberculosis H(37)Rv strain and antiviral activity in a series of cell cultures was evaluated. While the compounds were found to possess structure dependent cytostatic activity, these were not found to be efficient inhibitors of M. tuberculosis nor did they inhibit a broad variety of DNA or RNA viruses in cell culture. (C) 2011 Elsevier Masson SAS. All rights reserved.