4-amino-2-methylthio-6-(phenylethynyl)pyrimidine-5-carbaldehyde | 867193-35-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-amino-2-methylthio-6-(phenylethynyl)pyrimidine-5-carbaldehyde
• 英文别名: 4-amino-2-methylsulfanyl-6-(2-phenylethynyl)pyrimidine-5-carbaldehyde
• CAS: 867193-35-9
• 化学式: C₁₄H₁₁N₃OS
• 分子量: 269.327
• InChiKey: BJRTTZQJQJILGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-2-methylthio-6-(phenylethynyl)pyrimidine-5-carbaldehyde 在 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 以90%的产率得到4-amino-2-methylthio-7-phenylpyrido[4,3-d]pyrimidine 6-oxide
  参考文献：
  名称：

  Synthesis of 4-amino-7-phenylpyrido[4,3-d]pyrimidine 6-oxides

  摘要：

  DOI：

  10.1007/s10593-007-0079-9
• 作为产物：
  描述：

  4-氨基-6-氯-2-甲硫基嘧啶-5-甲醛 、 苯乙炔 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43%的产率得到4-amino-2-methylthio-6-(phenylethynyl)pyrimidine-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

• 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。
• Tandem reactions of 6-phenylethynylpyrimidine-5-carbaldehydes with alcohols: regioselective synthesis of 5-alkoxy-(7Z)-7-benzylidene-5,7-dihydrofuro[3,4-d]pyrimidines and 5-alkoxy-7-phenyl-5H-pyrano[4,3-d]pyrimidines
  作者：Inga Cikotiene、Rita Buksnaitiene、Simonas Rudys、Marius Morkunas、Dainius Motiejaitis

  DOI：10.1016/j.tet.2009.10.108

  日期：2010.1

  An efficient and versatile tandem processes of acetalisation and cycloisomerization reactions have been developed for the reactions of 6-phenylethynylpyrimidine-5-carbaldehydes. The influence of the catalyst and role of the substituent in the position 4 of the pyrimidine ring have been studied. Regioselective synthesis of 5,7-dihydrofuro[3,4-d]pyrimidine and pyrano[4,3-d]pyrimidine cores is described. (C) 2009 Elsevier Ltd. All rights reserved.
• Novel Method for Synthesis of Pyrido[4,3-d]pyrimidines
  作者：I. Susvilo、R. Palskyte、S. Tumkevicius、A. Brukstus

  DOI：10.1007/s10593-005-0142-3

  日期：2005.2
• 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.
• Synthesis of 4-amino-7-phenylpyrido[4,3-d]pyrimidine 6-oxides
  作者：N. Cikotiene、R. Buksnaitiene、A. Brukstus

  DOI：10.1007/s10593-007-0079-9

  日期：2007.4