2-benzyl-4-amino-5-ethoxycarbonyl-pyrimidine

• 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-benzyl-4-amino-5-ethoxycarbonyl-pyrimidine
• 英文别名: 4-amino-2-benzyl-5-ethoxycarbonylpyrimidine；ethyl 4-amino-2-benzylpyrimidine-5-carboxylate
• 化学式: C₁₄H₁₅N₃O₂
• mdl: MFCD26768558
• 分子量: 257.292
• InChiKey: KJYYDSUFIUCIMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  78.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-benzyl-4-amino-5-ethoxycarbonyl-pyrimidine 以 乙醇 为溶剂， 反应 20.0h， 生成 2-Amino-4-hydroxy-6-methylamino-5-phenylpyridine-3-carbaldehyde methylimine
  参考文献：
  名称：

  Recyclization reactions of 1-alkylpyrimidinium salts

  摘要：

  The reaction of 4-amino-2-benzyl-1-methyl-5-ethoxycarbonylpyrimidinium iodide (3) with alcoholic methylamine resulted in the formation of the methylimine of 2-amino-4-hydroxy-6-methylamino-5-phenylpyridine-3-carbaldehyde (5). Heating of the same pyrimidinium salt in benzylamine gave a mixture of products of two C-C recyclizations: 2-benzyl-4-benzylamino-5-carbamoylpyrimidine (7) and the benzylimine of 4-amino-2-benzyl-6-benzylaminopyrimidine-5-carbaldehyde (8). The reaction of 2-amino-1,4-dimethyl-5-ethoxycarbonylpyrimidinium iodide (10) with KOH ethanolic solution gave a single product of C-C-recyclization: 2-amino-5-acetyl-4-hydroxypyrimidine (11).

  DOI：

  10.1515/hc.2011.025
• 作为产物：
  描述：

  2-苯基盐酸乙脒盐酸盐 、 2-氰基-3-乙氧基丙烯酸乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 4.5h， 以47%的产率得到2-benzyl-4-amino-5-ethoxycarbonyl-pyrimidine
  参考文献：
  名称：

  Recyclization reactions of 1-alkylpyrimidinium salts

  摘要：

  The reaction of 4-amino-2-benzyl-1-methyl-5-ethoxycarbonylpyrimidinium iodide (3) with alcoholic methylamine resulted in the formation of the methylimine of 2-amino-4-hydroxy-6-methylamino-5-phenylpyridine-3-carbaldehyde (5). Heating of the same pyrimidinium salt in benzylamine gave a mixture of products of two C-C recyclizations: 2-benzyl-4-benzylamino-5-carbamoylpyrimidine (7) and the benzylimine of 4-amino-2-benzyl-6-benzylaminopyrimidine-5-carbaldehyde (8). The reaction of 2-amino-1,4-dimethyl-5-ethoxycarbonylpyrimidinium iodide (10) with KOH ethanolic solution gave a single product of C-C-recyclization: 2-amino-5-acetyl-4-hydroxypyrimidine (11).

  DOI：

  10.1515/hc.2011.025

文献信息

• Isomerization/recyclization of some 5-ethoxycarbonyl-pyrimidines
  作者：R. S. Vardanyan、V. J. Hruby、G. G. Danagulyan、A. D. Mkrtchyan

  DOI：10.1002/jhet.5570420413

  日期：2005.5

  This communication reports on the investigation of a new recyclization conversion of a pyrimidine ring, which can be referred to as CC recyclization. In this reaction the nucleophile cleaves the pyrimidine ring at the N(3)-C(4) bond, and following rotation around the single C(5)-C(6) bond the new cyclization takes place. This type of recyclization has general applicability, and takes place upon alkali

  该通讯报道了对嘧啶环新的环化转化的研究，这可以称为C C环化。在此反应中，亲核试剂在N（3）-C（4）键上切割嘧啶环，然后围绕单个C（5）-C（6）键旋转后发生新的环化反应。这种类型的再循环具有普遍的适用性，发生在碱处理取代的4-甲基-5-乙氧基羰基-和4-氨基-5-乙氧基羰基-嘧啶（1）时，分别转化成4-羟基-5-乙酰基-和4-羟基-5-氨基甲酰基嘧啶（2）。所获得的嘧啶基酮可以容易地转化为它们的7-12。
• 10.1023/b:cohc.0000014422.20094.d1
  作者：Danagulyan、Mkrtchyan

  DOI：10.1023/b:cohc.0000014422.20094.d1

  日期：——
• Recyclization reactions of 1-alkylpyrimidinium salts
  作者：Ruben S. Vardanyan、Gevork G. Danagulyan、Armen D. Mkrtchyan、Victor J. Hruby

  DOI：10.1515/hc.2011.025

  日期：2011.1.1

  The reaction of 4-amino-2-benzyl-1-methyl-5-ethoxycarbonylpyrimidinium iodide (3) with alcoholic methylamine resulted in the formation of the methylimine of 2-amino-4-hydroxy-6-methylamino-5-phenylpyridine-3-carbaldehyde (5). Heating of the same pyrimidinium salt in benzylamine gave a mixture of products of two C-C recyclizations: 2-benzyl-4-benzylamino-5-carbamoylpyrimidine (7) and the benzylimine of 4-amino-2-benzyl-6-benzylaminopyrimidine-5-carbaldehyde (8). The reaction of 2-amino-1,4-dimethyl-5-ethoxycarbonylpyrimidinium iodide (10) with KOH ethanolic solution gave a single product of C-C-recyclization: 2-amino-5-acetyl-4-hydroxypyrimidine (11).