2-(1H-咪唑-1-基)嘧啶 | 134914-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-(1H-咪唑-1-基)嘧啶
• 英文名称: 2-(1H-imidazol-1-yl)pyrimidine
• 英文别名: 2-imidazol-1-ylpyrimidine
• CAS: 134914-65-1
• 化学式: C₇H₆N₄
• mdl: MFCD08256102
• 分子量: 146.151
• InChiKey: WQMHSYISOHEFSU-UHFFFAOYSA-N

物化性质

• 熔点：
  124 °C
• 沸点：
  370.3±25.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-咪唑-1-基)嘧啶 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 2-(1H-imidazol-1-yl)-pyrimidine hydrochloride
  参考文献：
  名称：

  Synthesis, X-ray characterization and computational Studies of N-imidazolyl and N-pyrazolyl pyrimidine derivatives

  摘要：

  In this manuscript we report the synthesis and X-ray characterization of neutral 2-(1H-imidazol-1-yl)-pyrimidine (1), 2-(1H-pyrazol-1-yl)-pyrimidine (2) and 1-(2-pyrimidinyl)-1H-benzimidazole (3). We have also obtained crystals of the corresponding hydrochlorides of compounds 1 and 3. Finally, the outer sphere complex of protonated 2-(1H-imidazol-1-yl)-pyrimidine with [CoCl4](2-) as counterion is described. In several charged structures interesting anion-pi interactions determine the crystal packing. Moreover, in neutral systems some stacking interactions are governed by double lone pair-pi interactions. High level ab initio calculations (RI-MP2/def2-TZVP) have been used to evaluate the noncovalent interactions observed in the solid state and the interplay between them. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.023
• 作为产物：
  描述：

  咪唑 、 2-氯嘧啶 在 copper(l) iodide 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.5h， 以78%的产率得到2-(1H-咪唑-1-基)嘧啶
  参考文献：
  名称：

  Synthesis of Precursor Imidazolium Salts for the Synthesis of N-Heterocyclic Carbines Used as Ligands for the Enantioselective Preparation of Heterosteroids Compounds

  摘要：

  咪唑盐1-苯基-3-(3-(4,4,5,5-四甲基-1,3,2-二氧硼烷-2-基)丙基)-1H-咪唑-3-氢溴盐（4）和1-(嘧啶-2-基)-3-(3-(4,4,5,5-四甲基-1,3,2-二氧硼烷-2-基)丙基)-1H-咪唑-3-氢溴盐（5）是通过前体1-苯基-1H-咪唑（1）和2-(1H-咪唑-1-基)嘧啶（2）与2-(3-溴丙基)-4,4,5,5-四甲基-1,3,2-二氧硼烷（3）的偶联反应分别制备的。这些化合物的纯度通过光谱数据得到了确认。 NMR光谱显示了所有信号，结构通过高分辨率质谱（HRMS）得到了确认。

  DOI：

  10.13005/ojc/300204

文献信息

• 2-Aminopyrimidine-4,6-diol as an Efficient Ligand for Solvent-Free Copper-Catalyzed N-Arylations of Imidazoles with Aryl and Heteroaryl Halides
  作者：Ye-Xiang Xie、Shao-Feng Pi、Jian Wang、Du-Lin Yin、Jin-Heng Li

  DOI：10.1021/jo061572q

  日期：2006.10.1

  Efficient and solvent-free copper-catalyzed N-arylations of imidazoles with aryl and heteroaryl halides have been demonstrated. In the presence of CuBr, 2-aminopyrimidine-4,6-diol, and TBAF (n-Bu4NF), a variety of imidazoles underwent the N-arylation reaction with aryl and heteroaryl halides smoothly in moderate to excellent yields. Noteworthy is that the reaction is conducted under solvent-free conditions

  已经证明了咪唑与芳基和杂芳基卤化物的高效且无溶剂的铜催化的N-芳基化。在CuBr，2-氨基嘧啶-4,6-二醇和TBAF（n -Bu 4 NF）的存在下，各种咪唑与芳基和杂芳基卤化物的N-芳基化反应均以中等至优异的收率顺利进行。值得注意的是，该反应在无溶剂条件下进行。
• [EN] KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA KINASE
  申请人：LILLY CO ELI

  公开号：WO2005080380A1

  公开（公告）日：2005-09-01

  ABSTRACT The present invention provides kinase inhibitors of Formula I: .

  摘要 本发明提供了化合物I的激酶抑制剂。
• [EN] BENZIMIDAZOLES AND BENZOTHIAZOLES AS INHIBITORS OF MAP KINASE<br/>[FR] BENZIMIDAZOLES ET BENZOTHIAZOLES UTILISES COMME INHIBITEURS DE LA MAP KINASE
  申请人：LILLY CO ELI

  公开号：WO2004014900A1

  公开（公告）日：2004-02-19

  The present invention provides kinase inhibitors of Formula I: wherein W represents inter alia imidazol, oxazol, pyrazol, thiazol as triazol, which are substituted by phenyl or thienyl. The disclosed compounds inhibit p-38 kinase and are useful in the treatment of metastasis or rheumatoid arthritis.

  本发明提供了一种化合物I的激酶抑制剂：其中W代表咪唑、噁唑、吡唑、噻唑或三唑等，这些化合物被苯基或噻吩基取代。所公开的化合物抑制p-38激酶，在转移或类风湿性关节炎的治疗中很有用。
• Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation
  作者：Yuanguang Chen、Fangyu Du、Fengyang Chen、Qifan Zhou、Guoliang Chen

  DOI：10.1055/s-0039-1690702

  日期：2019.12

  selective N-arylation of amines or azoles with aryl halides­, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and

  在胺或唑与芳基卤的选择性N-芳基化反应中，发现甲基-α - d-吡喃葡萄糖苷（MG）作为铜粉的绿色配体起作用。另外，氮杂环胺化合物还可与杂环芳基氯进行N-芳基化偶联。该方法允许在温和的反应条件下获得各种芳族胺和芳基唑，具有良好的耐受性，并且以中等至高收率进行。
• Amination of Heteroaryl Chlorides: Palladium Catalysis or S_NAr in Green Solvents?
  作者：Katie Walsh、Helen F. Sneddon、Christopher J. Moody

  DOI：10.1002/cssc.201300239

  日期：2013.8

  reaction of heteroaryl chlorides in the pyrimidine, pyrazine and quinazoline series with amines in water in the presence of KF results in a facile SNAr reaction and N‐arylation. The reaction is less satisfactory with pyridines unless an additional electron‐withdrawing group is present. The results showed that the transition‐metal‐free SNAr reaction not only compares favourably to palladium‐catalysed

  嘧啶、吡嗪和喹唑啉系列中的杂芳基氯化物与水中的胺在 KF 存在下发生反应，导致容易的 S N Ar 反应和N芳基化。除非存在额外的吸电子基团，否则吡啶的反应不太令人满意。结果表明，无过渡金属的 S N Ar 反应不仅优于钯催化的偶联反应，而且在碱和溶剂方面也可以在环境可接受的（“绿色”）条件下进行。