2-amino-6-(3,3-dimethoxypropyl)-4-methyl-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester | 911857-40-4

• 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-amino-6-(3,3-dimethoxypropyl)-4-methyl-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester
• 英文别名: 3-O-tert-butyl 5-O-ethyl 2-amino-4-(3,3-dimethoxypropyl)-6-methyl-4H-pyrimidine-3,5-dicarboxylate
• CAS: 911857-40-4
• 化学式: C₁₈H₃₁N₃O₆
• 分子量: 385.461
• InChiKey: METGTEARTUZSKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-amino-6-(3,3-dimethoxypropyl)-4-methyl-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-ethyl ester 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Trifluoro-acetate1-amino-4-ethoxycarbonyl-7-methoxy-3-methyl-4a,5,6,7-tetrahydro-2H-pyrrolo[1,2-c]pyrimidin-8-ylium;
  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：

  4,4-二甲氧基丁醛 在 4-二甲氨基吡啶 、 氨 、 碳酸氢钠 、 氯化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 72.0h， 生成 2-amino-6-(3,3-dimethoxypropyl)-4-methyl-6H-pyrimidine-1,5-dicarboxylic acid 1-tert-butyl ester 5-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