4-chloro-6-(4-methoxyphenyl)-2-methylpyrimidine | 142220-68-6

• 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-6-(4-methoxyphenyl)-2-methylpyrimidine
• CAS: 142220-68-6
• 化学式: C₁₂H₁₁ClN₂O
• 分子量: 234.685
• InChiKey: VSTVDVFEVVXBSK-UHFFFAOYSA-N

物化性质

• 沸点：
  361.5±32.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-6-(4-methoxyphenyl)-2-methylpyrimidine 在 5%-palladium/activated carbon 、 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以89%的产率得到4-(4-methoxyphenyl)-2-methylpyrimidine
  参考文献：
  名称：

  Pyrimidine as an Aryl C–H Activating Group

  摘要：

  The Pd-catalyzed regioselective C-H activation/arylation, /iodination, and/acetoxylation reactions of 4-arylpyrimidines using aryl iodides, N-iodosuccinimide, and (diacetoxyiodo)benzene respectively as coupling partners are described. Suzuki-Miyaura coupling and Sonogashira reactions of the resulting aryl iodides are demonstrated. The scalability of the C-H activation/functionalization starting with readily accessible 4-aryl pyrimidines is also reported.

  DOI：

  10.1021/acs.orglett.8b01300
• 作为产物：
  描述：

  4,6-二氯-2-甲基嘧啶 、 4-甲氧基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 异丙醇 为溶剂， 反应 18.0h， 以80%的产率得到4-chloro-6-(4-methoxyphenyl)-2-methylpyrimidine
  参考文献：
  名称：

  Synthesis of 4-Aryl and Unsymmetrical 4,6-Diarylpyrimidines by the Suzuki-Miyaura Cross-Coupling Reaction

  摘要：

  A two-step procedure for the synthesis of 4-arylpyrimidines from inexpensive 4,6-dichloropyrimidine via a Suzuki-Miyaura/hydrodechlorination reaction sequence is described. The reaction resulted in the predominant formation of mono-arylated product. The cross-coupling of 4-chloro-6-substituted pyrimidines with various aryl/heteroarylboronic acids also furnished 4,6-disubstituted pyrimidines in acceptable yields.

  DOI：

  10.3987/com-18-13956

文献信息

• Pyrimidine derivatives and drugs
  申请人：Nippon Shinyaku Company, Limited

  公开号：US05589477A1

  公开（公告）日：1996-12-31

  The object of the present invention is to obtain new class of compounds which have improving effect on learning and memory disorders with good selectivity in central nervous system and little side effects and then to provide a good medicine for treatment of dementia. The present invention relates to the compounds represented by the following general formula or their pharmacologically acceptable salts and the drugs of improving learning or memory disorders comprising them as active ingredients. ##STR1## (wherein R.sup.1 and R.sup.2 are the same or different and are hydrogen, hydroxy, alkoxy, trifluoromethyl or halogen. A represents methyl, trifluoromethyl, or tert-butyl. Y represents O or NH.)

  本发明的目的是获得一类新化合物，其在中枢神经系统中具有改善学习和记忆障碍的作用，具有良好的选择性和少量副作用，然后提供一种治疗痴呆症的良好药物。本发明涉及以下一般式所代表的化合物或其药理学上可接受的盐以及包含它们作为活性成分的改善学习或记忆障碍的药物。##STR1##（其中R.sup.1和R.sup.2相同或不同，可以是氢、羟基、烷氧基、三氟甲基或卤素。A代表甲基、三氟甲基或叔丁基。Y代表氧或氨基。）
• PYRIMIDINE DERIVATIVE AND MEDICINE
  申请人：NIPPON SHINYAKU COMPANY, LIMITED

  公开号：EP0555478A1

  公开（公告）日：1993-08-18

  The invention aims at obtaining a novel compound which is excellent in central nervous system selectivity and reduced in side effects and has an activity of improving the function of learning and memory, thus providing an excellent medicine for dementia. The invention relates to a compound represented by general formula (I), a pharmacologically acceptable salt thereof, and an agent for remedying the disturbance of learning and memory containing the same as the active ingredient of formula (I), wherein R¹ and R² may be the same or different from each other and each represents hydrogen, hydroxy, alkoxy, trifluoromethyl or halogen; A represents methyl, trifluoromethyl or tertbutyl; and Y represents O or NH.

  本发明旨在获得一种新型化合物，该化合物具有良好的中枢神经系统选择性和较低的副作用，并具有改善学习和记忆功能的活性，从而提供了一种治疗痴呆症的良药。本发明涉及通式(I)代表的化合物、其药理上可接受的盐，以及含有通式(I)活性成分的治疗学习和记忆障碍的药物，其中R¹和R²可以相同或不同，各自代表氢、羟基、烷氧基、三氟甲基或卤素；A代表甲基、三氟甲基或叔丁基；Y代表O或NH。
• Synthesis of 4-Aryl and Unsymmetrical 4,6-Diarylpyrimidines by the Suzuki-Miyaura Cross-Coupling Reaction
  作者：Victor Snieckus、Gerald J. Tanoury、Sahaj Gupta、Jennifer A. Melanson、M Selim Hossain、Louis Vaillancourt、William A. Nugent

  DOI：10.3987/com-18-13956

  日期：——

  A two-step procedure for the synthesis of 4-arylpyrimidines from inexpensive 4,6-dichloropyrimidine via a Suzuki-Miyaura/hydrodechlorination reaction sequence is described. The reaction resulted in the predominant formation of mono-arylated product. The cross-coupling of 4-chloro-6-substituted pyrimidines with various aryl/heteroarylboronic acids also furnished 4,6-disubstituted pyrimidines in acceptable yields.
• US5589477A
  申请人：——

  公开号：US5589477A

  公开（公告）日：1996-12-31
• Pyrimidine as an Aryl C–H Activating Group
  作者：Sahaj Gupta、Jennifer A. Melanson、Louis Vaillancourt、William A. Nugent、Gerald J. Tanoury、Gabriele Schatte、Victor Snieckus

  DOI：10.1021/acs.orglett.8b01300

  日期：2018.7.6

  The Pd-catalyzed regioselective C-H activation/arylation, /iodination, and/acetoxylation reactions of 4-arylpyrimidines using aryl iodides, N-iodosuccinimide, and (diacetoxyiodo)benzene respectively as coupling partners are described. Suzuki-Miyaura coupling and Sonogashira reactions of the resulting aryl iodides are demonstrated. The scalability of the C-H activation/functionalization starting with readily accessible 4-aryl pyrimidines is also reported.