(4-chloro-2-methylsulfanyl-6-(piperidin-1-yl)pyrimidin-5-yl)phenylmethanol | 1393456-97-7

• 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-2-methylsulfanyl-6-(piperidin-1-yl)pyrimidin-5-yl)phenylmethanol
• 英文别名: (4-Chloro-2-(methylthio)-6-(piperidin-1-yl)pyrimidin-5-yl)(phenyl)methanol；(4-chloro-2-methylsulfanyl-6-piperidin-1-ylpyrimidin-5-yl)-phenylmethanol
• CAS: 1393456-97-7
• 化学式: C₁₇H₂₀ClN₃OS
• 分子量: 349.884
• InChiKey: TYNLVMLTKYKUCP-UHFFFAOYSA-N

物化性质

• 沸点：
  542.1±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (4-chloro-2-methylsulfanyl-6-(piperidin-1-yl)pyrimidin-5-yl)phenylmethanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到(4-chloro-2-methylsulfanyl-6-(piperidin-1-yl)pyrimidin-5-yl)phenylmethanone
  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
• 作为产物：
  描述：

  哌啶-1-甲醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.84h， 生成 (4-chloro-2-methylsulfanyl-6-(piperidin-1-yl)pyrimidin-5-yl)phenylmethanol
  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

• 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.