methyl 4-methyl-2-phenylpyrimidine-5-carboxylate | 773134-16-0

• 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: methyl 4-methyl-2-phenylpyrimidine-5-carboxylate
• CAS: 773134-16-0
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: VRHHIYHRZRUXLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-methyl-2-phenylpyrimidine-5-carboxylate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以100%的产率得到4-甲基-2-苯基-5-嘧啶甲酸
  参考文献：
  名称：

  Efficient Assembly of 2,5,6-Substituted Pyrimidines via MgI₂-Mediated Morita−Baylis−Hillman Reaction

  摘要：

  A mild and efficient protocol for the synthesis of a 2,6-disubstituted pyrimidine-5-carboxylate library via a Morita-Baylis-Hillman (MBH) adduct is described. Herein, the three step methodology involves the use of substituted alpha-iodomethylene beta-keto ester intermediates obtained after oxidation of the MBH adducts, which are condensed with various types of amidine or guanidine derivatives, to generate the 2, 6-disubstituted pyrimidines-5-carboxylate libraries.

  DOI：

  10.1021/cc100001e
• 作为产物：
  描述：

  、 苄脒盐酸盐 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 methyl 4-methyl-2-phenylpyrimidine-5-carboxylate
  参考文献：
  名称：

  Efficient Assembly of 2,5,6-Substituted Pyrimidines via MgI₂-Mediated Morita−Baylis−Hillman Reaction

  摘要：

  A mild and efficient protocol for the synthesis of a 2,6-disubstituted pyrimidine-5-carboxylate library via a Morita-Baylis-Hillman (MBH) adduct is described. Herein, the three step methodology involves the use of substituted alpha-iodomethylene beta-keto ester intermediates obtained after oxidation of the MBH adducts, which are condensed with various types of amidine or guanidine derivatives, to generate the 2, 6-disubstituted pyrimidines-5-carboxylate libraries.

  DOI：

  10.1021/cc100001e

文献信息

• Copper-Catalyzed One-pot Synthesis of Pyrimidines from Amides, <i>N</i> ,<i>N</i> ′-dimethylformamide dimethylacetal, and Enamines
  作者：Hitesh B. Jalani、Wangshui Cai、Hongjian Lu

  DOI：10.1002/adsc.201700234

  日期：2017.7.17

  versatile copper catalyzed one‐pot synthesis of diversely substituted pyrimidines directly from amides, N,N′‐dimethylformamide dimethylacetal (DMF−DMA) and enamines has been established. The reaction involved the two C−N bonds and one C−C bond formation by formal [2+1+3] annulation approach to pyrimidines. This protocol is based on the use of readily available primary amides, DMF−DMA and enamines to

  直接从酰胺，N，N'-二甲基甲酰胺二甲基乙缩醛（DMF-DMA）和烯胺中直接建立了多种取代的嘧啶的通用铜催化单锅合成方法。该反应涉及通过对嘧啶的正式[2 + 1 + 3]环化方法形成的两个CN键和一个CC键。该协议基于使用现成的伯酰胺，DMF-DMA和烯胺以单锅方式安装具有多种功能的二取代和三取代嘧啶结构的方法，这使该策略对药物化学具有吸引力。
• Mechanistic Insights into the Reaction of Amidines with 1,2,3-Triazines and 1,2,3,5-Tetrazines
  作者：Zhi-Chen Wu、K. N. Houk、Dale L. Boger、Dennis Svatunek

  DOI：10.1021/jacs.2c03726

  日期：2022.6.22

  initial nucleophilic attack of an amidine on azine C4, with a subsequent energetically favored N2 elimination step compared with a disfavored stepwise formation of a Diels–Alder cycloadduct. The proposed reaction mechanism is in agreement with experimental and computational results, which explains the observed reactivity of 1,2,3-triazines and 1,2,3,5-tetrazines with amidines.

  1,2,3-三嗪和 1,2,3,5-四嗪与脒快速、高效、选择性地反应生成嘧啶/1,3,5-三嗪，与 1,2,4,5 具有正交反应性-基于四嗪的共轭化学。虽然异构体 1,2,4-三嗪和 1,2,4,5-四嗪与烯烃的反应机理已广为人知，但 1,2,3-三嗪/1,2,3, 5-四嗪-脒反应及其内在反应性仍未得到充分探索。通过使用15 N 标记、动力学研究和动力学同位素效应研究，辅以广泛的计算研究，我们表明该反应通过添加/N 2进行消除/环化途径，而不是通常预期的协同或逐步 Diels-Alder/复古 Diels-Alder 序列。该转化中的限速步骤是脒对吖嗪 C4 的初始亲核攻击，随后是能量有利的 N 2消除步骤，而不是 Diels-Alder 环加合物的逐步形成。所提出的反应机理与实验和计算结果一致，这解释了观察到的 1,2,3-三嗪和 1,2,3,5-四嗪与脒的反应性。
• Efficient Assembly of 2,5,6-Substituted Pyrimidines via MgI₂-Mediated Morita−Baylis−Hillman Reaction
  作者：Vasudha Sharma、Mark L. McLaughlin

  DOI：10.1021/cc100001e

  日期：2010.5.10

  A mild and efficient protocol for the synthesis of a 2,6-disubstituted pyrimidine-5-carboxylate library via a Morita-Baylis-Hillman (MBH) adduct is described. Herein, the three step methodology involves the use of substituted alpha-iodomethylene beta-keto ester intermediates obtained after oxidation of the MBH adducts, which are condensed with various types of amidine or guanidine derivatives, to generate the 2, 6-disubstituted pyrimidines-5-carboxylate libraries.