2-(4-chloro-6-methylpyrimidin-2-yl)aminoethyl acetate | 873842-27-4

• 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-(4-chloro-6-methylpyrimidin-2-yl)aminoethyl acetate
• 英文别名: 2-(2-Acetoxyethyl)amino-4-chloro-6-methylpyrimidine；2-[(4-chloro-6-methylpyrimidin-2-yl)amino]ethyl acetate
• CAS: 873842-27-4
• 化学式: C₉H₁₂ClN₃O₂
• 分子量: 229.666
• InChiKey: NPCYOGZUBIIKAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-6-methylpyrimidin-2-yl)aminoethyl acetate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 以43%的产率得到2-(2-acetoxyethyl)amino-5-bromo-6-methyl-4-chloropyrimidine
  参考文献：
  名称：

  Effect of halogen atom localization on the level of antimycobacterial activity of 2-amino-4-arylamino-6-methylpyrimidines

  摘要：

  Several hydrochlorides of 2-alkyl(cycloalkyl, aralkyl)-5-bromo-6-methyl-4-phenylaminopyrimidines have been synthesized as isosteric analogs of the corresponding 2-alkyl(cycloalkyl, aralkyl)-4-(3-bromophenyl)amino-6-methylpyrimidine hydrochlorides. Moving the bromine atom from the benzene ring into the heterocycle is accompanied by a significant decrease in the level of antimycobacterial activity.

  DOI：

  10.1134/s1070363210040237
• 作为产物：
  描述：

  6-甲基-4-羟基-2-甲硫基嘧啶 在 吡啶 、 三氯氧磷 作用下， 反应 4.0h， 生成 2-(4-chloro-6-methylpyrimidin-2-yl)aminoethyl acetate
  参考文献：
  名称：

  异胞嘧啶的多功能衍生物。水合对2-（2-羟乙基）氨基-6-甲基嘧啶-4（3 H ）-one质子互变异构的影响

  摘要：

  2-（2-羟乙基）氨基-6-甲基嘧啶-4（ 3H ）-的水合 形成4-氧代-3,4-二氢和4-羟基互变异构体的平衡混合物。这些互变异构体相互过渡的中间体具有两性离子结构。随着介质极性的降低，平衡转变为4-氧代-3,4-二氢形式。

  DOI：

  10.1007/s11176-005-0287-x

文献信息

• 4-arylamino-2-(2-acetoxyethyl)amino-6-methylpyrimidines: Synthesis, deacetylation, and biological activity
  作者：A. V. Erkin、V. I. Krutikov

  DOI：10.1134/s1070363207110163

  日期：2007.11

  The reaction of 2-(2-acetoxyethyl)amino-4-chloro-6-methylpyrimidine with aromatic amines leads to a series of 4-arylamino-2-(2-acetoxyethyl)amino-6-methylpyrimidines. Deacetylation of these compounds proceeds in both acidic and basic media. Most of the arylaminopyrimides obtained exhibit a pronounced antituberculous effect.
• Polyfunctional isocytosine derivatives: II. Regioselectivity of methylation of 2-(2-hydroxyethylamino)-6-methylpyrimidin-4(3H)-one in different media
  作者：A. V. Erkin、V. I. Krutikov

  DOI：10.1134/s1070363206030194

  日期：2006.3

  High regioselectivity in the methylation of 2-(2-hydroxyethylamino)-6-methylpyrimidin-4(3H)C, one at the N-3 atom in water and ethanol in the presence of inorganic bases is determined by participation of the oxygen atom in hydrogen bonding and its coordination to metal cation, respectively. In going to aprotic dimethylformamide which is capable of solvating cations, the regioselectivity decreases, and a mixture of N-3- and O-methyl isomers is formed.