6-氨基-1-甲基-2-氧代-1,2-二氢-5-嘧啶甲醛 | 154867-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-氨基-1-甲基-2-氧代-1,2-二氢-5-嘧啶甲醛
• 英文名称: 4-amino-3-methyl-2-oxo-2,3-dihydropyrimidine-5-carbaldehyde
• 英文别名: 6-Amino-1-methyl-2-oxo-1,2-dihydropyrimidine-5-carbaldehyde；6-amino-1-methyl-2-oxopyrimidine-5-carbaldehyde
• CAS: 154867-32-0
• 化学式: C₆H₇N₃O₂
• 分子量: 153.14
• InChiKey: FENUGAJMXNCRGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-二甲基苯并肼 、 6-氨基-1-甲基-2-氧代-1,2-二氢-5-嘧啶甲醛 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Deshmukh, M. B.; Shelar, M. A.; Mittelbach, M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 5, p. 491 - 493

  摘要：

  DOI：
• 作为产物：
  描述：

  2-formyl-3-(3-methylureido)propenenitrile 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以55%的产率得到6-氨基-1-甲基-2-氧代-1,2-二氢-5-嘧啶甲醛
  参考文献：
  名称：

  Synthesis with Nitriles: 92. Synthesis of 5-Formylcytosine Derivatives

  摘要：

  The reactivity of 3-dimethylamino-2-formylpropenenitrile (1) with various amino compounds is studied. Thus, condensation of 1 with anilines gives the corresponding azomethines (2a-c). Reaction of 1 with thiourea and guanidne resp., leads to 5-formylthiocytosine (3) and 2-amino-5-cyanopyrimidine (4). The 2-formyl-3-ureidopropenenitriles (5a-i) can be obtained by reaction of 1 with urea and substituted ureas. 5a-i can easily be cyclized to 3-substituted 5-formylcytosines (6-e). Condensation of 6 with aniline, benzylamine and phenylhydrazine leads to the azomethines (7a-i). Pyrido [ 2,3-d ] pyrimidine-6-carbonitriles (8a, 8b, Sd and 83) are obtained by reaction of 6 with malononitrile.

  DOI：

  10.3987/com-93-6416

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.
• Deshmukh, M. B.; Shelar, M. A.; Mittelbach, M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 5, p. 491 - 493
  作者：Deshmukh, M. B.、Shelar, M. A.、Mittelbach, M.、Junek, H.

  DOI：——

  日期：——
• Synthesis with Nitriles: 92. Synthesis of 5-Formylcytosine Derivatives
  作者：Madhukar Jachak、Martin Mittelbach、Hans Junek

  DOI：10.3987/com-93-6416

  日期：——

  The reactivity of 3-dimethylamino-2-formylpropenenitrile (1) with various amino compounds is studied. Thus, condensation of 1 with anilines gives the corresponding azomethines (2a-c). Reaction of 1 with thiourea and guanidne resp., leads to 5-formylthiocytosine (3) and 2-amino-5-cyanopyrimidine (4). The 2-formyl-3-ureidopropenenitriles (5a-i) can be obtained by reaction of 1 with urea and substituted ureas. 5a-i can easily be cyclized to 3-substituted 5-formylcytosines (6-e). Condensation of 6 with aniline, benzylamine and phenylhydrazine leads to the azomethines (7a-i). Pyrido [ 2,3-d ] pyrimidine-6-carbonitriles (8a, 8b, Sd and 83) are obtained by reaction of 6 with malononitrile.