5-bromo-2-(2-hydroxyethyl)amino-6-methyl-4-oxodihydro-3H-pyrimidine | 33238-64-1

• 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: 5-bromo-2-(2-hydroxyethyl)amino-6-methyl-4-oxodihydro-3H-pyrimidine
• 英文别名: 5-Brom-2-(2-hydroxyethylamino)-6-methyl-4(3H)-pyrimidinon；5-bromo-2-(2-hydroxyethyl)amino-6-methylpyrimidin-4(3H)-one；5-bromo-2-(2-hydroxy-ethylamino)-6-methyl-3H-pyrimidin-4-one；5-Bromo-2-(2-hydroxyethyl)amino-6-methylpyrimidin-4(3h)-one；5-bromo-2-(2-hydroxyethylamino)-4-methyl-1H-pyrimidin-6-one
• CAS: 33238-64-1
• 化学式: C₇H₁₀BrN₃O₂
• 分子量: 248.079
• InChiKey: QDBPSSRTRYTCGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  73.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(2-hydroxyethyl)amino-6-methyl-4-oxodihydro-3H-pyrimidine 在 吡啶 、 五氯化磷 作用下， 生成 2-(2-acetoxyethyl)amino-5-bromo-6-methyl-4-phenylaminopyrimidine hydrochloride
  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：

  2-(2-hydroxy-ethylamino)-6-methylpyrimidin-4(3H)-one 在 溴 、 溶剂黄146 作用下， 以78%的产率得到5-bromo-2-(2-hydroxyethyl)amino-6-methyl-4-oxodihydro-3H-pyrimidine
  参考文献：
  名称：

  Polyfunctional Derivatives of Isocytosine: I. Intramolecular Rearrangement of 6-Methyl-4-oxo-2-[2-(phenylcarbamoyloxy)ethyl]aminodihydro-3H-pyrimidine

  摘要：

  2-(2-羟乙基)氨基-6-甲基-4-氧代二氢-3H-嘧啶与苯基异氰酸酯的反应生成6-甲基-4-氧代-2-[2-(苯基氨基甲酰氧基)乙基]二氢-3H-嘧啶，在盐酸的作用下，该化合物重新排列为2-(2-羟乙基)氨基-6-甲基-4-氧代-5-苯基氨基甲酰二氢-3H-嘧啶。

  DOI：

  10.1007/s11176-005-0516-3

文献信息

• Effect of halogen atom localization on the level of antimycobacterial activity of 2-amino-4-arylamino-6-methylpyrimidines
  作者：A. V. Erkin、V. I. Krutikov

  DOI：10.1134/s1070363210040237

  日期：2010.4

  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.
• Polyfunctional Derivatives of Isocytosine: I. Intramolecular Rearrangement of 6-Methyl-4-oxo-2-[2-(phenylcarbamoyloxy)ethyl]aminodihydro-3H-pyrimidine
  作者：A. V. Erkin、V. I. Krutikov、A. V. Kosykh

  DOI：10.1007/s11176-005-0516-3

  日期：2005.11

  The reaction of 2-(2-hydroxyethyl)amino-6-methyl-4-oxodihydro-3H-pyrimidine with phenyl isocyanate yields 6-methyl-4-oxo-2-[2-(phenylcarbamoyloxy)ethyl]dihydro-3H-pyrimidine, which rearranges into 2-(2-hydroxyethyl)amino-6-methyl-4-oxo-5-phenylcarbamoyldihydro-3H-pyrimidine under the action of HCl.

  2-(2-羟乙基)氨基-6-甲基-4-氧代二氢-3H-嘧啶与苯基异氰酸酯的反应生成6-甲基-4-氧代-2-[2-(苯基氨基甲酰氧基)乙基]二氢-3H-嘧啶，在盐酸的作用下，该化合物重新排列为2-(2-羟乙基)氨基-6-甲基-4-氧代-5-苯基氨基甲酰二氢-3H-嘧啶。