4-chloro-6-dimethylamino-2-methylsulfanylpyrimidine-5-carboxaldehyde | 445040-58-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-chloro-6-dimethylamino-2-methylsulfanylpyrimidine-5-carboxaldehyde
• 英文别名: 6-chloro-4-dimethylamino-2-methylthiopyrimidine-5-carbaldehyde；4-Chloro-6-(dimethylamino)-2-(methylthio)pyrimidine-5-carbaldehyde；4-chloro-6-(dimethylamino)-2-methylsulfanylpyrimidine-5-carbaldehyde
• CAS: 445040-58-4
• 化学式: C₈H₁₀ClN₃OS
• 分子量: 231.706
• InChiKey: LLBHOLZLLXNOBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  388.5±37.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-chloro-6-dimethylamino-2-methylsulfanylpyrimidine-5-carboxaldehyde 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以61%的产率得到4-dimethylamino-6-methylthioisoxazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  Kaminskas; Dailide; Tumkevicius, Polish Journal of Chemistry, 2002, vol. 76, # 5, p. 725 - 728

  摘要：

  DOI：
• 作为产物：
  描述：

  4,6-二氯-二甲硫基嘧啶 、 N,N-二甲基甲酰胺 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.67h， 以75%的产率得到4-chloro-6-dimethylamino-2-methylsulfanylpyrimidine-5-carboxaldehyde
  参考文献：
  名称：

  Synthesis of 5,6-Disubstituted Thieno[2,3-d]pyrimidines from 4-Chloropyrimidines

  摘要：

  Facile reaction sequences for the preparation of 5,6-disubstituted thieno[2,3-d]pyrimidines starting with 4-chloropyrimidines have been developed. 4-Chloro-6-methoxypyrimidines were aroylated at the 5-positions via lithiation with LDA and subsequent treatment with benzaldehyde or N-methoxy-N-methylbenzamides to give aryl(4-chloro-6-methoxypyrimidin-5-yl)methanones. These pyrimidinyl ketones were transformed in one-pot into 5,6-disubstituted 4-methoxythieno[2,3-d]pyrimidines by a successive treatment with sodium sulfide, BrCH(2)EWGs, and sodium hydride. Lithiation of 4,6-dichloro-2-(methylsulfanyl)pyrimidine at the 5-position was followed by treatment with tertiary formamides to give 4-chloro-6-(dialkylamino)pyrimidine-5-carboxaldehydes, which could be transformed into 5,6-disubstituted 4-(dialkylamino)thieno[2,3-d]pyrimidines via aryl [4-chloro-6-(dialkylamino)pyrimidin-5-yl]methanones using the same one-pot thiophene ring forming sequence.

  DOI：

  10.3987/com-12-12463

文献信息

• 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.
• Novel cyclocondensation of 2-acylethynyl-1-amino- and 2-alkoxycarbonylethynyl-1-amino-anthraquinones with pyridines
  作者：I. I. Barabanov

  DOI：10.1007/s10593-005-0083-x

  日期：2004.11
• ——
  作者：S. Tumkevicius、A. Kaminskas

  DOI：10.1023/a:1025114703659

  日期：——
• Synthesis of 5,6-Disubstituted Thieno[2,3-d]pyrimidines from 4-Chloropyrimidines
  作者：Kazuhiro Kobayashi、Teruhiko Suzuki、Taketoshi Kozuki、Naoki Matsumoto、Hidetaka Hiyoshi、Kazuto Umezu

  DOI：10.3987/com-12-12463

  日期：——

  Facile reaction sequences for the preparation of 5,6-disubstituted thieno[2,3-d]pyrimidines starting with 4-chloropyrimidines have been developed. 4-Chloro-6-methoxypyrimidines were aroylated at the 5-positions via lithiation with LDA and subsequent treatment with benzaldehyde or N-methoxy-N-methylbenzamides to give aryl(4-chloro-6-methoxypyrimidin-5-yl)methanones. These pyrimidinyl ketones were transformed in one-pot into 5,6-disubstituted 4-methoxythieno[2,3-d]pyrimidines by a successive treatment with sodium sulfide, BrCH(2)EWGs, and sodium hydride. Lithiation of 4,6-dichloro-2-(methylsulfanyl)pyrimidine at the 5-position was followed by treatment with tertiary formamides to give 4-chloro-6-(dialkylamino)pyrimidine-5-carboxaldehydes, which could be transformed into 5,6-disubstituted 4-(dialkylamino)thieno[2,3-d]pyrimidines via aryl [4-chloro-6-(dialkylamino)pyrimidin-5-yl]methanones using the same one-pot thiophene ring forming sequence.
• Kaminskas; Dailide; Tumkevicius, Polish Journal of Chemistry, 2002, vol. 76, # 5, p. 725 - 728
  作者：Kaminskas、Dailide、Tumkevicius

  DOI：——

  日期：——