4-chloro-5-iodo-2,6-dimethoxypyrimidine | 134221-53-7

• 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: 4-chloro-5-iodo-2,6-dimethoxypyrimidine
• CAS: 134221-53-7
• 化学式: C₆H₆ClIN₂O₂
• 分子量: 300.483
• InChiKey: XCUWJUCSKOUCEN-UHFFFAOYSA-N

物化性质

• 熔点：
  127 °C
• 沸点：
  80 °C(Press: 0.1 Torr)
• 密度：
  1.902±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-5-iodo-2,6-dimethoxypyrimidine 在 四(三苯基膦)钯 copper(l) iodide 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.5h， 生成 6-(5-Ethynyl-2,6-dimethoxy-pyrimidin-4-yl)-hex-5-yn-1-ol
  参考文献：
  名称：

  Photochemical and Thermal Bergman Cyclization of a Pyrimidine Enediynol and Enediynone

  摘要：

  Novel 10-membered pyrimidine enediynes (3 and 4) were synthesized in seven and eight steps, respectively. These compounds were compared for their abilities to undergo Bergman cyclization both thermally and photochemically, Alcohol 3 readily cyclized both thermally and photochemically in (PrOH)-Pr-i, while ketone 4 only showed efficient thermal cyclization, Both compounds were also shown to cleave dsDNA under the appropriate conditions.

  DOI：

  10.1021/ol006061j
• 作为产物：
  描述：

  2,4-dimethoxy-6-chloro-5-lithium-pyrimidine 以86%的产率得到
  参考文献：
  名称：

  PLE, N.;TURCK, A.;FIQUET, E.;QUEGUINER, G., J. HETEROCYCL. CHEM., 28,(1991) N, C. 283-287

  摘要：

  DOI：

文献信息

• Preparation of Polyfunctionalized 2,6-Dimethoxypyrimidine Derivatives via Chemo- and Regioselective Direct Zinc Insertion
  作者：Paul Knochel、Darunee Soorukram、Nadège Boudet、Vladimir Malakhov

  DOI：10.1055/s-2007-983885

  日期：2007.12

  direct chemo- and regioselective zinc insertions is described. The insertion of commercially available zinc dust into C-I and C-Br bonds, in the presence of LiCl, proceeded under mild reaction conditions. The reactions of the resulting organozinc reagents with electrophiles gave the expected products in good yields. This procedure represents a new method for the polyfunctionalization of uracil derivatives

  描述了通过直接化学选择性和区域选择性锌插入在 2,6-二甲氧基嘧啶衍生物的 C4 和/或 C5 位置进行的功能化。在 LiCl 存在下，将市售的锌粉插入 CI 和 C-Br 键中，是在温和的反应条件下进行的。所得有机锌试剂与亲电试剂的反应以良好的产率产生预期的产物。该程序代表了尿嘧啶衍生物多官能化的新方法。
• Preparation of Polyfunctional Arylzinc Organometallics in Toluene by Halogen/Zinc Exchange Reactions
  作者：Moritz Balkenhohl、Dorothée S. Ziegler、Alexandre Desaintjean、Leonie J. Bole、Alan R. Kennedy、Eva Hevia、Paul Knochel

  DOI：10.1002/anie.201906898

  日期：2019.9.9

  toluene within 10 min to 5 h through an I/Zn or Br/Zn exchange reaction using bimetallic reagents of the general formula R'2 Zn⋅2 LiOR (R'=sBu, tBu, pTol). Highly sensitive functional groups, such as a triazine, a ketone, an aldehyde, or a nitro group, were tolerated in these exchange reactions, enabling the synthesis of a plethora of functionalized (hetero)arenes after quenching with various electrophiles

  使用通式R'2Zn⋅2LiOR（R'= sBu）的双金属试剂，通过I / Zn或Br / Zn交换反应，在10分钟至5小时内，在甲苯中制备了多种多官能的二芳基和二杂芳基锌物质。 ，tBu，pTol）。在这些交换反应中可以耐受高度敏感的官能团，例如三嗪，酮，醛或硝基，从而可以在用各种亲电试剂淬灭后合成大量官能化的（杂）芳烃。对这些双金属混合物的组成和反应性的深入了解揭示了[R'2 Zn（OR）2 Li2]型高活性二有机二烷氧基锌酸锂的形成。
• Metallation of diazines.<b>III</b>. New synthesis of analogues of trimethoprim and of bacimethrin
  作者：N. Ple、A. Turck、E. Fiquet、G. Queguiner

  DOI：10.1002/jhet.5570280213

  日期：1991.2

  6-dimethoxypyrimidine was lithiated by lithium 2,2,6,6-tetramethylpiperidide. The resulting lithio derivative was submitted to reaction with carbonyl derivatives, iodine and trimethyltin chloride. Synthesis of analogues of trimethoprim and of bacimetrin are reported.

  通过2,2,6,6-四甲基哌啶锂对4-氯-2,6-二甲氧基嘧啶进行锂化。使所得的硫代衍生物与羰基衍生物，碘和三甲基氯化锡反应。据报道合成了甲氧苄氨嘧啶和巴西咪坦的类似物。
• Rapid Bergman Cyclization of 1,2-Diethynylheteroarenes
  作者：Chang-Sik Kim、K. C. Russell

  DOI：10.1021/jo980879p

  日期：1998.11.1

  The synthesis and cyclization of acyclic quinoxaline, pyridine, and pyrimidine enediynes (1-3) are described. These compounds were prepared using palladium(0) coupling of trimethylsilyl acetylene to o-dihalo- or o-halotriflic heteroarenes. All compounds were prepared in modest to good yields. The enediynes prepared were shown to undergo Bergman cyclization. Kinetics over a minimum of 3 half-lives were used to construct Arrhenius plots. Pyrimidine 3 was found to have an activation energy of 16.1 kcal/mol. Cyclization of the closest known aromatic analogue, o-diethynylbenzene (15), has E-a = 25.1 kcal/mol (Grissom, J. W.; Calkins, T. L.;McMillen, H. A.; Jiang, Y. J. Org. Chem. 1994, 59, 5833-5835). Pyridine 2 and quinoxaline 1 gave activation energies of 21.5 and 33.6 kcal/mol, respectively. The results illustrate that heteroarenes can be used to activate Bergman cyclization. We expect these compounds to play an important role in furthering the understanding of Bergman cyclization and in aiding the development of new biologically significant enediynes.