6-methyl-4-phenylsulfanyl-1,4-dihydro-pyrimidine-5-carboxylic acid ethyl ester

• 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: 6-methyl-4-phenylsulfanyl-1,4-dihydro-pyrimidine-5-carboxylic acid ethyl ester
• 英文别名: 2-(phenylthio)-1,4-dihydropyrimidine；Ethyl 6-methyl-4-phenyl-2-phenylsulfanyl-1,4-dihydropyrimidine-5-carboxylate
• 化学式: C₂₀H₂₀N₂O₂S
• 分子量: 352.457
• InChiKey: HIPHRDDKBBFBNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯硼酸 、 6-methyl-4-phenylsulfanyl-1,4-dihydro-pyrimidine-5-carboxylic acid ethyl ester 在 噻吩-2-甲酸亚铜(I) 、 双(2-二苯基磷苯基)醚 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以65%的产率得到ethyl 2,4-diphenyl-6-methyl-1,4-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Wool-anchored Pd(OAc)₂ complex: a highly active and reusable catalyst for desulfurative coupling reactions

  摘要：

  一种生物大分子锚定的钯配合物，羊毛-Pd(OAc)₂，被用作催化剂，用于Liebeskind–Srogl去硫偶联反应，将嘧啶基硫醚衍生物与末端炔烃和芳基硼酸进行偶联。

  DOI：

  10.1039/c5cy00802f
• 作为产物：
  描述：

  苯甲醛 在 盐酸 、 copper diacetate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 6-methyl-4-phenylsulfanyl-1,4-dihydro-pyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Nano copper oxide mediated ligand-free C–S cross-coupling and concomitant oxidative aromatization of 4-aryl-3,4-dihydropyrimidin-2(1H)-thione with diaryliodonium salts

  摘要：

  A wide range of Biginelli 4-aryl-3,4-dihydropyrimidin-2(1H)-thiones undergo ligand-free C-S cross-coupling with diaryliodonium triflates in the presence of CuO nanoparticles with the concomitant oxidative aromatization to form highly substituted 2-(thioaryl)pyrimidine. The nano CuO catalyst can be recycled and reused three times without any significant loss of catalytic activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.131

文献信息

• Palladium(0)-Catalyzed, Copper(I)-Mediated Coupling of Boronic Acids with Cyclic Thioamides. Selective Carbon−Carbon Bond Formation for the Functionalization of Heterocycles^†
  作者：Hana Prokopcová、C. Oliver Kappe

  DOI：10.1021/jo070408f

  日期：2007.6.1

  Employing controlled microwave irradiation at 100 °C, most cross-couplings can be completed within 2 h and proceed in high yields. An advantage of using thioamides as starting materials is the fact that the system can be tuned to an alternative carbon−sulfur cross-coupling pathway by changing to stoichiometric copper(II) under oxidative conditions. Both types of thioamide cross-couplings are orthogonal to

  描述了在化学计量的铜（I）辅因子存在下，钯催化的环硫酰胺与芳基硼酸的交叉偶联。脱硫碳-碳交叉偶联方案是在中性条件下进行的，可应用于具有嵌入的硫酰胺片段的杂环结构。成功的碳-碳交叉偶联与环大小，芳香性/非芳香性，起始硫酰胺结构中是否存在其他杂原子或其他官能团无关。通过在100°C下控制微波辐射，大多数交叉偶联可在2 h内完成，并以高收率进行。使用硫代酰胺作为起始原料的一个优点是，可以通过在氧化条件下更改为化学计量的铜（II），将系统调节至另一种碳-硫交叉偶联途径。两种类型的硫酰胺交叉偶联均与芳烃卤化物与硼酸的传统碱催化的Suzuki-Miyaura交叉偶联正交。
• Tunable Carbon−Carbon and Carbon−Sulfur Cross-Coupling of Boronic Acids with 3,4-Dihydropyrimidine-2-thiones
  作者：Alenka Lengar、C. Oliver Kappe

  DOI：10.1021/ol036496h

  日期：2004.3.1

  Direct microwave-assisted Pd(0)-catalyzed/Cu(I)-mediated carbon-carbon cross-coupling of 3,4-dihydropyrimidine-2-thiones and boronic acids under Liebeskind-Srogl conditions leads to 2-aryl-1,4-dihydropyrimidines in moderate to high yield. In contrast, Cu(II)-mediated reaction of the same substrates leads to carbon-sulfur cross-coupling. [reaction: see text]

  Liebeskind-Srogl条件下3,4-二氢嘧啶-2-硫酮与硼酸的直接微波辅助Pd（0）催化/ Cu（I）介导的碳-碳交叉偶联导致2-芳基-1,4 -二氢嘧啶，中等至高产率。相反，相同底物的Cu（II）介导的反应导致碳-硫交叉偶联。[反应：看文字]
• Pd-Catalyzed Regioselective Tandem C–S/C–N Bond Formation for Modular Synthesis of Pyrimidine-Fused Benzothiazoles from o-Dihaloarenes and 3,4-Dihydropyrimidin-2-thiones
  作者：Chunxia Chen、Jinsong Peng、Xuying Hu、Ruiqi Liu、Shiwen Fu、Lianxu Shi

  DOI：10.1055/a-2311-3930

  日期：2024.7

  A Pd-catalyzed annulation reaction for the synthesis of 4H-pyrimido[2,1-b]benzothiazole derivatives via regioselective tandem C-S/C-N bond formation was developed. With PdCl2(PPh3)2 as the precatalyst, Davephos as the ligand, and K2CO3 as the base, various 3,4-dihydropyrimidin-2-thiones with o-dihaloarenes proceeded smoothly, and the desired products were obtained in moderate to good yields