5-(4'-aminophenyl)-6-isopropyl-pyrimidine-2,4-diamine | 634199-53-4

• 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: 5-(4'-aminophenyl)-6-isopropyl-pyrimidine-2,4-diamine
• 英文别名: 5-(4-Aminophenyl)-6-propan-2-ylpyrimidine-2,4-diamine
• CAS: 634199-53-4
• 化学式: C₁₃H₁₇N₅
• 分子量: 243.311
• InChiKey: VDRBFSVTCMJZQB-UHFFFAOYSA-N

物化性质

• 熔点：
  218-219 °C
• 沸点：
  506.7±60.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对甲砜基苯甲醛 、 5-(4'-aminophenyl)-6-isopropyl-pyrimidine-2,4-diamine 在 sodium acetate 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以70%的产率得到6-isopropyl-5-(4-{[4-(methylsulfonyl)benzyl]amino}phenyl)pyrimidine-2,4-diamine
  参考文献：
  名称：

  Optimization of 2,4-diaminopyrimidines as GHS-R antagonists: Side chain exploration

  摘要：

  The synthesis and structure-activity relationships of the 4- and 6-substituents of 2,4-diaminopyrimidine-based growth hormone secretagogue receptor (GHS-R) antagonists are described. Diaminopyrimidines with 6-norbornenyl (4n) and 6-tetrahydrofuranyl (4p) substitutents were found to exhibit potent GHS-R antagonism and good selectivity (similar to 1000-fold) against dihydrofolate reductase. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.012
• 作为产物：
  描述：

  对硝基苯乙腈 在 palladium dihydroxide 4-二甲氨基吡啶 、 氢气 、 三乙胺 、 三甲基硅烷化重氮甲烷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 5-(4'-aminophenyl)-6-isopropyl-pyrimidine-2,4-diamine
  参考文献：
  名称：

  Optimization of 2,4-diaminopyrimidines as GHS-R antagonists: Side chain exploration

  摘要：

  The synthesis and structure-activity relationships of the 4- and 6-substituents of 2,4-diaminopyrimidine-based growth hormone secretagogue receptor (GHS-R) antagonists are described. Diaminopyrimidines with 6-norbornenyl (4n) and 6-tetrahydrofuranyl (4p) substitutents were found to exhibit potent GHS-R antagonism and good selectivity (similar to 1000-fold) against dihydrofolate reductase. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.012

文献信息

• An Expeditious Synthesis of 6-Alkyl-5-(4′-amino-phenyl)-pyrimidine-2,4-diamines
  作者：Daniel D. Holsworth、Michael Stier Jeremy、J. Edmunds、Wei He、Samuel Place、Samarendra Maiti

  DOI：10.1081/scc-120024725

  日期：2003.10

  Abstract A rapid synthesis of a series of 6-alkyl substituted-5-(4′-amino-phenyl)-pyrimidine-2,4-diamines is described. These analogs were produced in good yields on moderate scale (ca. 8 g) without chromatography. Furthermore, the methodology described herein allows the production of 6-[ethyl, propyl, isopropyl, and isobutyl]-5-(4′-amino-phenyl)-pyrimidine-2,4-diamines in a more straightforward manner

  摘要描述了一系列 6-烷基取代的-5-(4'-氨基-苯基)-嘧啶-2,4-二胺的快速合成。这些类似物在没有色谱法的情况下以中等规模（约 8 克）的良好收率生产。此外，本文所述的方法允许以比先前公开的更直接的方式生产 6-[乙基、丙基、异丙基和异丁基]-5-(4'-氨基-苯基)-嘧啶-2,4-二胺。 [1d] 这些新型化合物应该有助于对当前具有抗肿瘤和抗疟疾活性的嘧啶进行构效关系分析。
• Optimization of 2,4-diaminopyrimidines as GHS-R antagonists: Side chain exploration
  作者：Bo Liu、Mei Liu、Zhili Xin、Hongyu Zhao、Michael D. Serby、Christi Kosogof、Lissa T.J. Nelson、Bruce G. Szczepankiewicz、Wiweka Kaszubska、Verlyn G. Schaefer、H. Douglas Falls、Chun Wel Lin、Christine A. Collins、Hing L. Sham、Gang Liu

  DOI：10.1016/j.bmcl.2006.01.012

  日期：2006.4

  The synthesis and structure-activity relationships of the 4- and 6-substituents of 2,4-diaminopyrimidine-based growth hormone secretagogue receptor (GHS-R) antagonists are described. Diaminopyrimidines with 6-norbornenyl (4n) and 6-tetrahydrofuranyl (4p) substitutents were found to exhibit potent GHS-R antagonism and good selectivity (similar to 1000-fold) against dihydrofolate reductase. (C) 2006 Elsevier Ltd. All rights reserved.