(4-chloro-6-dimethylamino-2-methylsulfanylpyrimidin-5-yl)(4-methoxyphenyl)methanone | 1393457-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-chloro-6-dimethylamino-2-methylsulfanylpyrimidin-5-yl)(4-methoxyphenyl)methanone
• CAS: 1393457-00-5
• 化学式: C₁₅H₁₆ClN₃O₂S
• 分子量: 337.83
• InChiKey: AABLYAMBWGLHNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.32
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  溴乙酸叔丁酯 、 (4-chloro-6-dimethylamino-2-methylsulfanylpyrimidin-5-yl)(4-methoxyphenyl)methanone 在 sodium sulfide 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 oil 为溶剂， 反应 1.42h， 以46%的产率得到tert-butyl 4-(dimethylamino)-5-(4-methoxyphenyl)-2-(methylthio)thieno[2,3-d]pyrimidine-6-carboxylate
  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：

  4-chloro-6-dimethylamino-2-methylsulfanylpyrimidine-5-carboxaldehyde 在 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 (4-chloro-6-dimethylamino-2-methylsulfanylpyrimidin-5-yl)(4-methoxyphenyl)methanone
  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