3-(5-Chloro-2-methanesulfonyl-pyrimidin-4-yl)-2-(1-methyl-1H-benzoimidazol-2-yl)-3-oxo-propionitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 3-(5-Chloro-2-methanesulfonyl-pyrimidin-4-yl)-2-(1-methyl-1H-benzoimidazol-2-yl)-3-oxo-propionitrile
• 英文别名: 3-(5-Chloro-2-methylsulfonylpyrimidin-4-yl)-2-(1-methylbenzimidazol-2-yl)-3-oxopropanenitrile
• 化学式: C₁₆H₁₂ClN₅O₃S
• 分子量: 389.822
• InChiKey: WEVWLZGTBRBACK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(5-Chloro-2-methanesulfonyl-pyrimidin-4-yl)-2-(1-methyl-1H-benzoimidazol-2-yl)-3-oxo-propionitrile 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以92%的产率得到7-methyl-3-(methylsulfonyl)-5-oxo-5,7-dihydrobenzo[4',5']imidazo[2',1':6,1]pyrido[3,2-d]pyrimidine-6-carbonitrile
  参考文献：
  名称：

  Nucleophilic Substitution in Some 5-Chloropyrimidines. Synthesis and Properties of Condensed Pyridopyrimidines

  摘要：

  Reaction of hetarylacetonitriles 1 with 5-chloro-2-(methylsulfonyl)-4-pyrimidinecarbonyl chloride affords a series of new ketonitriles 3e-h. The reactions of compounds 3 with aliphatic amines were studied. In the reaction of 3c, d, g with aliphatic amines the replacement of methylsulfonyl group took place to give products 4. In the reaction of 3a with aliphatic amines 3-(NRR2)-R-1-5-oxo-5H-pyrimido-[4,5-c]quinolizin-6-yl cyanides 5a-d were formed. Compounds 3 cyclized into fused pyridopyrimidines 6-10 in the presence of Et3N and the displacement of methylsulfonyl group in 6, 7, 9 by amines was investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00181-2