N2-Boc-9-butyl-6-chloro-9H-purin-2-ylamine | 1175562-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N2-Boc-9-butyl-6-chloro-9H-purin-2-ylamine
• 英文别名: tert-butyl N-(9-butyl-6-chloropurin-2-yl)carbamate
• CAS: 1175562-15-8
• 化学式: C₁₄H₂₀ClN₅O₂
• 分子量: 325.798
• InChiKey: HVLLUVXIHFYVGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N2-Boc-9-butyl-6-chloro-9H-purin-2-ylamine 在 甲酸 作用下， 以 水 为溶剂， 反应 2.0h， 以95%的产率得到2-氨基-9-丁基-3H-嘌呤-6-酮
  参考文献：
  名称：

  Concise access to N9-mono-, N2-mono- and N2,N9-di-substituted guanines via efficient Mitsunobu reactions

  摘要：

  Guanine poses several problems to the synthetic chemist owing to its polyfunctional nature and poor solubility. Over the past few decades, synthetic guanines have found applications as anti-cancer and anti-viral agents. Coupled with the ever-growing interest in designer PNAs and G-quartets, simple and efficient synthetic routes to novel guanines would be of significant benefit. We herein report that, upon simple protection and/or activation step(s), the guanine precursor 2-amino-6-chloropurine is rendered an excellent substrate for Mitsunobu chemistry, furnishing, after subsequent hydrolytic dechlorination and appropriate deprotection step(s), the desired N9-mono-, N2-mono- or N2,N9-di-substituted guanines in excellent yields (>= 80%). Importantly, we demonstrate that N9-functionalization proceeds with very good N9/N7 regioselectivity and with complete inversion of stereochemistry. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.118
• 作为产物：
  描述：

  tert-butyl (6-chloro-9H-purin-2-yl)carbamate 、 正丁醇 在 三苯基膦 、 偶氮二甲酸二异丙酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.28h， 以88%的产率得到N2-Boc-9-butyl-6-chloro-9H-purin-2-ylamine
  参考文献：
  名称：

  通过顺序的N9，N2 Mitsunobu反应轻松有效地获得2,6,9-三取代嘌呤

  摘要：

  提出了一种2,6,9-三取代嘌呤的简便，有效和温和的合成方法，从市售的2-氨基-6-氯嘌呤开始，其采用先后顺序的N9然后N2 Mitsunobu反应作为关键步骤。重要的是，我们对嘌呤核进行N2官能化的合成方法消除了用伯胺将2-卤基团进行传统亲核芳香取代所需要的苛刻条件。在两次光延反应中，苯甲酸，烯丙基，炔丙基和脂肪族醇的收率都非常好。显着地，对于第一次偶联观察到优异的化学选择性和N9-区域选择性，并且在室温下15分钟内反应完成。我们新颖的方法很容易适应提供N 9-单-或N2，N 9-二官能化的鸟嘌呤类似物，并且我们的方案的实用性通过CDK抑制剂波西米因的有效合成得到进一步证明。

  DOI：

  10.1016/j.tetlet.2009.04.137

文献信息

• Concise access to N9-mono-, N2-mono- and N2,N9-di-substituted guanines via efficient Mitsunobu reactions
  作者：Steven Fletcher、Vijay M. Shahani、Alan J. Lough、Patrick T. Gunning

  DOI：10.1016/j.tet.2010.03.118

  日期：2010.6

  Guanine poses several problems to the synthetic chemist owing to its polyfunctional nature and poor solubility. Over the past few decades, synthetic guanines have found applications as anti-cancer and anti-viral agents. Coupled with the ever-growing interest in designer PNAs and G-quartets, simple and efficient synthetic routes to novel guanines would be of significant benefit. We herein report that, upon simple protection and/or activation step(s), the guanine precursor 2-amino-6-chloropurine is rendered an excellent substrate for Mitsunobu chemistry, furnishing, after subsequent hydrolytic dechlorination and appropriate deprotection step(s), the desired N9-mono-, N2-mono- or N2,N9-di-substituted guanines in excellent yields (>= 80%). Importantly, we demonstrate that N9-functionalization proceeds with very good N9/N7 regioselectivity and with complete inversion of stereochemistry. (C) 2010 Elsevier Ltd. All rights reserved.
• Facile and efficient access to 2,6,9-tri-substituted purines through sequential N9, N2 Mitsunobu reactions
  作者：Steven Fletcher、Vijay M. Shahani、Patrick T. Gunning

  DOI：10.1016/j.tetlet.2009.04.137

  日期：2009.7

  both Mitsunobu reactions. Significantly, excellent chemoselectivity and N9-regioselectivity were observed for the first coupling, and reactions were complete within 15 min at room temperature. Our novel methodology may be readily adapted to furnish N9-mono- or N2,N9-di-functionalized guanine analogues, and the utility of our protocol is further demonstrated by the efficient synthesis of the CDK inhibitor

  提出了一种2,6,9-三取代嘌呤的简便，有效和温和的合成方法，从市售的2-氨基-6-氯嘌呤开始，其采用先后顺序的N9然后N2 Mitsunobu反应作为关键步骤。重要的是，我们对嘌呤核进行N2官能化的合成方法消除了用伯胺将2-卤基团进行传统亲核芳香取代所需要的苛刻条件。在两次光延反应中，苯甲酸，烯丙基，炔丙基和脂肪族醇的收率都非常好。显着地，对于第一次偶联观察到优异的化学选择性和N9-区域选择性，并且在室温下15分钟内反应完成。我们新颖的方法很容易适应提供N 9-单-或N2，N 9-二官能化的鸟嘌呤类似物，并且我们的方案的实用性通过CDK抑制剂波西米因的有效合成得到进一步证明。