6-(4-fluorophenyl)ethynyl-2-methylthio-4-pyrrolidin-1-ylpyrimidine-5-carbaldehyde | 1104638-81-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-(4-fluorophenyl)ethynyl-2-methylthio-4-pyrrolidin-1-ylpyrimidine-5-carbaldehyde
• 英文别名: 4-[2-(4-Fluorophenyl)ethynyl]-2-methylsulfanyl-6-pyrrolidin-1-ylpyrimidine-5-carbaldehyde
• CAS: 1104638-81-4
• 化学式: C₁₈H₁₆FN₃OS
• 分子量: 341.409
• InChiKey: GYNHNDXXBTWCEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(4-fluorophenyl)ethynyl-2-methylthio-4-pyrrolidin-1-ylpyrimidine-5-carbaldehyde 在 叔丁胺 作用下， 反应 24.0h， 以92%的产率得到7-(4-fluorophenyl)-2-methylthio-4-pyrrolidin-1-ylpyrido[4,3-d]pyrimidine
  参考文献：
  名称：

  An Efficient One-Pot Synthetic Method for 2,4-Disubstituted 7-Arylpyrido[4,3-d]pyrimidines from 2,4-Disubstituted 6-(Arylethynyl)pyrimidine-5-carbaldehydes and tert-Butylamine

  摘要：

  2,4-二取代的6-(芳基-乙炔基)嘧啶-5-甲醛与叔丁胺发生意外的热环化，在不存在的情况下以良好的收率得到2,4-二取代的7-芳基吡啶并[4,3-d]嘧啶任何催化剂。分离了中间体化合物并讨论了可能的反应机理。

  DOI：

  10.1055/s-0028-1083500
• 作为产物：
  描述：

  4-氟苯乙炔 、 4-氯-2-甲基磺酰基-6-吡咯烷-1-基-嘧啶-5-甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到6-(4-fluorophenyl)ethynyl-2-methylthio-4-pyrrolidin-1-ylpyrimidine-5-carbaldehyde
  参考文献：
  名称：

  Study on the cyclization of 6-arylethynylpyrimidine-5-carbaldehydes with tert-butylamine: microwave versus thermal preparation of pyrido[4,3-d]pyrimidines

  摘要：

  Thermal and microwave initiated cyclization of 2,4-disubstituted 6-arylethynylpyrimidine-5-carbaldehydes with tert-butylamine has been studied. A novel high-yielding preparation of 2,4-disubstituted 7-arylpyrido[4,3-d]pyrimidines has been developed. The intermediate compounds were isolated and possible mechanism of the reactions is discussed. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.015

文献信息

• An Efficient One-Pot Synthetic Method for 2,4-Disubstituted 7-Arylpyrido[4,3-<i>d</i>]pyrimidines from 2,4-Disubstituted 6-(Arylethynyl)pyrimidine-5-carbaldehydes and <i>tert</i>-Butylamine
  作者：Inga Cikotiene、Marius Morkunas、Simonas Rudys、Rita Buksnaitiene、Algirdas Brukstus

  DOI：10.1055/s-0028-1083500

  日期：——

  Unexpected thermal cyclization of 2,4-disubstituted 6-(aryl-ethynyl)pyrimidine-5-carbaldehydes with tert-butylamine proceeded to give 2,4-disubstituted 7-arylpyrido[4,3-d]pyrimidines in good yields in the absence of any catalysts. The intermediate compounds were isolated and possible mechanism of the reactions is discussed.

  2,4-二取代的6-(芳基-乙炔基)嘧啶-5-甲醛与叔丁胺发生意外的热环化，在不存在的情况下以良好的收率得到2,4-二取代的7-芳基吡啶并[4,3-d]嘧啶任何催化剂。分离了中间体化合物并讨论了可能的反应机理。
• The First and Efficient Synthesis of 7-Aryl-6-methoxycarbonylquinazolines via Unexpected Reaction of 6-Arylethynylpyrimidine-5-carbaldehydes and Methyl Mercaptoacetate
  作者：Inga Cikotiene、Marius Morkunas

  DOI：10.1055/s-0028-1087514

  日期：——

  A highly concise synthesis of 7-aryl-6-methoxycarbonylquinazolines via reaction of 6-arylethynylpyrimidine-5-carbaldehydes and methyl mercaptoacetate is described.

  描述了通过 6-芳基乙炔基嘧啶-5-甲醛和巯基乙酸甲酯的反应高度简洁地合成 7-芳基-6-甲氧基羰基喹唑啉。
• Study on the cyclization of 6-arylethynylpyrimidine-5-carbaldehydes with tert-butylamine: microwave versus thermal preparation of pyrido[4,3-d]pyrimidines
  作者：Inga Cikotiene、Visvaldas Kairys、Rita Buksnaitiene、Marius Morkunas、Simonas Rudys、Algirdas Brukstus、Miguel X. Fernandes

  DOI：10.1016/j.tet.2009.05.015

  日期：2009.7

  Thermal and microwave initiated cyclization of 2,4-disubstituted 6-arylethynylpyrimidine-5-carbaldehydes with tert-butylamine has been studied. A novel high-yielding preparation of 2,4-disubstituted 7-arylpyrido[4,3-d]pyrimidines has been developed. The intermediate compounds were isolated and possible mechanism of the reactions is discussed. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.