ethyl 6-azidomethyl-4-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 1017486-12-2

• 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: ethyl 6-azidomethyl-4-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 6-(azidomethyl)-4-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 1017486-12-2
• 化学式: C₉H₁₃N₅O₃
• 分子量: 239.234
• InChiKey: NWZBVOBTUCVPKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 6-azidomethyl-4-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以75%的产率得到ethyl 6-(aminomethyl)-4-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  A Facile Synthesis of Functionalized 1,2,6,7-Tetrahydroimidazo[1,5-c]pyrimidine-3,5-diones

  摘要：

  A Pd-mediated hydrogenation of ethyl 6-azidomethyl-1,2,3,4-tetrahydro-4-R-2-oxo-5-pyrimidinecarboxylates leads to the corresponding ethyl 6-aminomethyl1,2,3,4-tetrahydro-4-R-2-oxo-5-pyrimidinecarboxylates. The latter react with bis(trichloromethyl)carbonate, yielding the title ethyl 1,2,3,5,6,7-hexahydro-7-R-3,5-dioxoimidazo[1,5-c]pyrimidine-8-carboxylates. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.707738
• 作为产物：
  描述：

  ethyl 6-(bromomethyl)-2-oxo-4-methyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 sodium azide 、 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以62%的产率得到ethyl 6-azidomethyl-4-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Synthesis of new polyfunctional 5,6,7,8-tetrahydroimidazo-[1,5-c]pyrimidin-5-ones by the aza-Wittig reaction followed by intramolecular cyclization and 1,3-prototropic shift

  摘要：

  Ethyl 2-oxo-6-[(triphenyl-lambda(5)-phosphanylidene)aminomethyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylates reacted with organic isocyanates according to the aza-Wittig pattern, and the subsequent intramolecular ring closure and 1,3-H shift resulted in the formation of ethyl 3-alkyl(aryl)amino-5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-8-carboxylates.

  DOI：

  10.1134/s1070428009060207