2-(3,5-dimethyl-4-oxo-[1,3,5]triazin-1-yl)-6-methyl-4-phenyl-1,4-dihydropyrimidine-5-carboxylic acid ethyl ester | 911857-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(3,5-dimethyl-4-oxo-[1,3,5]triazin-1-yl)-6-methyl-4-phenyl-1,4-dihydropyrimidine-5-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-(3,5-dimethyl-4-oxo-1,3,5-triazinan-1-yl)-6-methyl-4-phenyl-1,4-dihydropyrimidine-5-carboxylate
• CAS: 911857-19-7
• 化学式: C₁₉H₂₅N₅O₃
• 分子量: 371.439
• InChiKey: WTJIRHDCGRLSBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,5-dimethyl-4-oxo-[1,3,5]triazin-1-yl)-6-methyl-4-phenyl-1,4-dihydropyrimidine-5-carboxylic acid ethyl ester 在 盐酸 作用下， 反应 24.0h， 以84%的产率得到5-ethoxycarbonyl-6-methyl-4-phenyl-3,4-dihydro-1H-pyrimidin-2-ylidene-ammonium chloride
  参考文献：
  名称：

  Concise Synthesis of Guanidine-Containing Heterocycles Using the Biginelli Reaction

  摘要：

  Two general methods for the synthesis of 2-imino-5-carboxy-3,4-dihydropyrimidines were developed using the three-component Biginelli reaction. The first method utilizes pyrazole carboxamidine, a beta-ketoester, and an aldehyde in an initial Biginelli reaction. After Boc protection, these products undergo aminolysis and acidic deprotection to generate 2-imino-5-carboxy-3,4-dihydropyrimidines in a four-step sequence. The second method utilizes a triazone-protected guanidine, a beta-ketoester, and an aldehyde in a Biginelli reaction. Acidic cleavage of the triazone yields 2-imino-5-carboxy-3,4-dihydropyrimidines in a two-step sequence. We also describe the further elaboration of several of these products using a tethered Biginelli reaction to give triazaacenaphthalene structures similar to those found in crambescidin and batzelladine alkaloids.

  DOI：

  10.1021/jo061199m
• 作为产物：
  描述：

  5-benzyl-1,3-dimethyl-[1,3,5]triazinan-2-one 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~70.0 ℃ 、5.17 MPa 条件下， 反应 65.0h， 生成 2-(3,5-dimethyl-4-oxo-[1,3,5]triazin-1-yl)-6-methyl-4-phenyl-1,4-dihydropyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Concise Synthesis of Guanidine-Containing Heterocycles Using the Biginelli Reaction

  摘要：

  Two general methods for the synthesis of 2-imino-5-carboxy-3,4-dihydropyrimidines were developed using the three-component Biginelli reaction. The first method utilizes pyrazole carboxamidine, a beta-ketoester, and an aldehyde in an initial Biginelli reaction. After Boc protection, these products undergo aminolysis and acidic deprotection to generate 2-imino-5-carboxy-3,4-dihydropyrimidines in a four-step sequence. The second method utilizes a triazone-protected guanidine, a beta-ketoester, and an aldehyde in a Biginelli reaction. Acidic cleavage of the triazone yields 2-imino-5-carboxy-3,4-dihydropyrimidines in a two-step sequence. We also describe the further elaboration of several of these products using a tethered Biginelli reaction to give triazaacenaphthalene structures similar to those found in crambescidin and batzelladine alkaloids.

  DOI：

  10.1021/jo061199m

文献信息

• Concise Synthesis of Guanidine-Containing Heterocycles Using the Biginelli Reaction
  作者：Bradley L. Nilsson、Larry E. Overman

  DOI：10.1021/jo061199m

  日期：2006.9.1

  Two general methods for the synthesis of 2-imino-5-carboxy-3,4-dihydropyrimidines were developed using the three-component Biginelli reaction. The first method utilizes pyrazole carboxamidine, a beta-ketoester, and an aldehyde in an initial Biginelli reaction. After Boc protection, these products undergo aminolysis and acidic deprotection to generate 2-imino-5-carboxy-3,4-dihydropyrimidines in a four-step sequence. The second method utilizes a triazone-protected guanidine, a beta-ketoester, and an aldehyde in a Biginelli reaction. Acidic cleavage of the triazone yields 2-imino-5-carboxy-3,4-dihydropyrimidines in a two-step sequence. We also describe the further elaboration of several of these products using a tethered Biginelli reaction to give triazaacenaphthalene structures similar to those found in crambescidin and batzelladine alkaloids.