1-ethyl-6-amino-2-oxo-1,2-dihydro-pyrimidine-5-carboxylic acid ethyl ester | 168428-16-8

• 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: 1-ethyl-6-amino-2-oxo-1,2-dihydro-pyrimidine-5-carboxylic acid ethyl ester
• 英文别名: 1-Aethyl-6-amino-2-oxo-1,2-dihydro-pyrimidin-5-carbonsaeure-aethylester；5-Carbethoxycytosine ethyl ester；ethyl 6-amino-1-ethyl-2-oxopyrimidine-5-carboxylate
• CAS: 168428-16-8
• 化学式: C₉H₁₃N₃O₃
• 分子量: 211.221
• InChiKey: BVOILXFBDGXBML-UHFFFAOYSA-N

物化性质

• 沸点：
  335.0±52.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  85
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-ethyl-6-amino-2-oxo-1,2-dihydro-pyrimidine-5-carboxylic acid ethyl ester 在 亚硝酸异戊酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以50%的产率得到3-ethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Syntheses with nitriles, XCV: Deamination of cytosine derivatives

  摘要：

  Treatment of 2-formyl-3-dimethylamino-propenenitrile (1a) and 2-ethoxycarbonyl-3-dimethylamino-propenenitrile (1b), resp., with substituted ureas led to the 2-cyano-3-ureidoacrylates 2, which can be cyclized under alkaline conditions to give 5-formyl-5-cyano-, and 5-alkoxycarbonyl-2-oxopyrimidine derivatives 3, 6, and 7. Reaction of 3 with isopentylnitrite gave a mixture of the deaminated and oxidized product 4 and the oxo derivative 5, which was acetalized during the separation step. Similar reaction with the alkoxycarbonyl derivatives 7 led to the formation of 1-alkyl-5-alkoxycarbonyl-pyrimidine-2,6-diones 8a-d.

  DOI：

  10.1007/bf00811761
• 作为产物：
  描述：

  3-(N'-ethyl-ureido)-2-cyano-acrylic acid ethyl ester 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以55%的产率得到1-ethyl-6-amino-2-oxo-1,2-dihydro-pyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Syntheses with nitriles, XCV: Deamination of cytosine derivatives

  摘要：

  Treatment of 2-formyl-3-dimethylamino-propenenitrile (1a) and 2-ethoxycarbonyl-3-dimethylamino-propenenitrile (1b), resp., with substituted ureas led to the 2-cyano-3-ureidoacrylates 2, which can be cyclized under alkaline conditions to give 5-formyl-5-cyano-, and 5-alkoxycarbonyl-2-oxopyrimidine derivatives 3, 6, and 7. Reaction of 3 with isopentylnitrite gave a mixture of the deaminated and oxidized product 4 and the oxo derivative 5, which was acetalized during the separation step. Similar reaction with the alkoxycarbonyl derivatives 7 led to the formation of 1-alkyl-5-alkoxycarbonyl-pyrimidine-2,6-diones 8a-d.

  DOI：

  10.1007/bf00811761

文献信息

• Syntheses with nitriles, XCV: Deamination of cytosine derivatives
  作者：M. Deshmukh、M. Mittelbach、H. Junek

  DOI：10.1007/bf00811761

  日期：1995.1

  Treatment of 2-formyl-3-dimethylamino-propenenitrile (1a) and 2-ethoxycarbonyl-3-dimethylamino-propenenitrile (1b), resp., with substituted ureas led to the 2-cyano-3-ureidoacrylates 2, which can be cyclized under alkaline conditions to give 5-formyl-5-cyano-, and 5-alkoxycarbonyl-2-oxopyrimidine derivatives 3, 6, and 7. Reaction of 3 with isopentylnitrite gave a mixture of the deaminated and oxidized product 4 and the oxo derivative 5, which was acetalized during the separation step. Similar reaction with the alkoxycarbonyl derivatives 7 led to the formation of 1-alkyl-5-alkoxycarbonyl-pyrimidine-2,6-diones 8a-d.