ethyl 2-amino-4-methyl-6-phenylpyrimidine-5-carboxylate | 928118-96-1

• 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-amino-4-methyl-6-phenylpyrimidine-5-carboxylate
• 英文别名: 2-amino-4-methyl-6-phenylpyrimidine-5-carboxylic acid ethyl ester
• CAS: 928118-96-1
• 化学式: C₁₄H₁₅N₃O₂
• 分子量: 257.292
• InChiKey: GKLKNSVXVXZKHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-4-methyl-6-phenylpyrimidine-5-carboxylate 、 在 噻吩-2-甲酸亚铜(I) 、 1,3-双(二苯基膦)丙烷 、 palladium diacetate 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以57%的产率得到
  参考文献：
  名称：

  二杂芳基二硫化物与杂环胺的钯催化C-N交叉偶联反应

  摘要：

  1，2-二（嘧啶-2-基）二硫化物与杂环胺（包括2-氨基嘧啶和1,3,4-噻二唑-2-胺）的Pd催化交叉偶联反应可提供对称的C-N偶联产物据报道产量中等至良好。该方法为合成具有杂环基序的生物活性分子和可药用化合物提供了机会。报告的协议显示出良好的官能团兼容性，并提供了一种从杂环二硫化物制备C2氨基嘧啶衍生物的新策略。

  DOI：

  10.1002/aoc.4020
• 作为产物：
  描述：

  ethyl 2-chloro-4-methyl-6-phenylpyrimidine-5-carboxylate 在 氨 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以80%的产率得到ethyl 2-amino-4-methyl-6-phenylpyrimidine-5-carboxylate
  参考文献：
  名称：

  Facile transformation of Biginelli pyrimidin-2(1H)-ones to pyrimidines. In vitro evaluation as inhibitors of Mycobacterium tuberculosis and modulators of cytostatic activity

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2011.03.010

文献信息

• Direct amination of pyrimidin-2-yl tosylates with aqueous ammonia under metal-free and mild conditions
  作者：Hai-Peng Gong、Yue Zhang、Yu-Xia Da、Zhang Zhang、Zheng-Jun Quan、Xi-Cun Wang

  DOI：10.1016/j.cclet.2015.01.034

  日期：2015.6

  A metal-free synthesis of pyrimidine functionalized primary amines via direct amination of pyrimidin-2-yl tosylate with aqueous ammonia has been developed under mild conditions. The desired products pyrimidin-2-amines can be generated in excellent yields in PEG-400, without any catalysts or other additives.

  在温和的条件下，已经开发了通过嘧啶-2-基甲苯磺酸酯与氨水直接胺化的嘧啶官能化伯胺的无金属合成方法。不需要任何催化剂或其他添加剂，即可在PEG-400中以优异的收率生成所需的嘧啶2-2-胺产物。
• Heterogenized hybrid catalyst of 1-sulfonic acid-3-methyl imidazolium ferric chloride over NaY zeolite for one-pot synthesis of 2-amino-4-arylpyrimidine derivatives: A viable approach
  作者：Pinky Gogoi、Arup Kumar Dutta、Susmita Saikia、Ruli Borah

  DOI：10.1016/j.apcata.2016.06.015

  日期：2016.8

  A new hybrid material of NaY zeolite supported 1-sulfonic acid-3-methyl imidazolium ferric chloride [Msim][FeCl4] has been developed by modifying the zeolite surface with six different w/w ratios through wet impregnation method. These composites were fully characterized by Powder XRD, FT-IR, Raman, TGA, SEM, TEM, EDX, BET, ICP-OES and Hammett acid strength measurement methods. The zeolite framework was found to be remaining preserved up to w/w ratio of 0.2 with some portion of extra framework Al species (EFAI) while crystallinity of the composites decreased from lower to higher loading. The overall thermal stability of composite materials increases up to w/w ratio of 0.1 than NaY. The catalytic performance of composite materials were examined for the novel one-pot consecutive formation of Biginelli- 3,4-dihydropyrimidin-2-(1H)-ones to 2-amino-4-arylpyrimidines. The 0.1 ratio composite material showed excellent catalytic activity up to ten consecutive cycles in solvent-free medium under the optimized reaction condition. (C) 2016 Elsevier B.V. All rights reserved.