2-(7-氯-3H-吡唑并[4,3-d]嘧啶-3-基)乙醇 | 64127-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 中文名称: 2-(7-氯-3H-吡唑并[4,3-d]嘧啶-3-基)乙醇
• 英文名称: 2-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethanol
• 英文别名: 2-{4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl}ethan-1-ol；2-(4-chloropyrazolo[3,4-d]pyrimidin-1-yl)ethanol
• CAS: 64127-15-7
• 化学式: C₇H₇ClN₄O
• mdl: MFCD12022632
• 分子量: 198.612
• InChiKey: CKGXWXQNFGKLIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(7-氯-3H-吡唑并[4,3-d]嘧啶-3-基)乙醇 、 2-肼基乙醇 、 邻氨基苯甲酸 、 4,6-二氯-5-嘧啶甲醛 生成 2-<1-(2-Hydroxy-aethyl)-pyrazolo<3,4-d>pyrimidin-4-ylamino>-benzoesaeure
  参考文献：
  名称：

  2-(Substituted heterocyclic amine)benzoic acids

  摘要：

  杂环化合物的公式为：##STR1## 其中Y和Z中的一个为CH，另一个为N，A为直链或支链饱和碳链，范围从C.sub.2到C.sub.6，X为氯、羟基、烷氧基或烷硫基，每个范围从C.sub.1到C.sub.5，R为氢、烷基、羟基烷基或二羟基烷基，每个范围从C.sub.1到C.sub.3，R'为卤素、烷基或烷氧基，每个范围从C.sub.1到C.sub.3，n为0、1或2。这些化合物及其光学异构体和生理耐受盐被用作药物，特别用于治疗中枢神经系统疾病。

  公开号：

  US04100286A1
• 作为产物：
  描述：

  2-肼基乙醇 、 4,6-二氯-5-嘧啶甲醛 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以31%的产率得到2-(7-氯-3H-吡唑并[4,3-d]嘧啶-3-基)乙醇
  参考文献：
  名称：

  1-烷基吡唑并[5,4- d ]嘧啶的一步合成

  摘要：

  描述了一种新的1-烷基吡唑并[5,4- d ]嘧啶的合成方法。4，6-二氯嘧啶-5-甲醛与各种取代的肼的反应可从市售原料中一步完成这些化合物。该方法相对于文献中当前描述的用于构造这种环系统的方法具有优势。

  DOI：

  10.1016/j.tetlet.2008.10.065

文献信息

• A short synthesis of 4-substituted 1-(hydroxyalkyl)-1H-pyrazolo[3,4-d]pyrimidines
  作者：Boulos Zacharie、Timothy P. Connolly、Rabindra Rej、Giorgio Attardo、Christopher L. Penney

  DOI：10.1016/0040-4020(95)01060-2

  日期：1996.2

  A simple and practical procedure was developed for the preparation of 4-substituted-1-(hydroxyalkyl)-1H-pyrazolo[3,4-d]pyrimidines. This was achieved by reacting nucleobase 3a or 3b with cesium carbonate or DBU in the presence of various alkyl iodides at 0°C in DMF. This procedure appears to be of general utility, proceeds in reasonable yield, and is applicable to different alkyl chain lengths including

  开发了一种简单而实用的方法来制备4-取代的-1-（羟烷基）-1H-吡唑并[3,4-d]嘧啶。这是通过使核碱基3a或3b与碳酸铯或DBU在0℃下于DMF中在各种烷基碘的存在下反应来实现的。该方法看来是通用的，以合理的产率进行，并且适用于不同的烷基链长，包括保护的和未保护的醇。这种方法的合成效用通过ST 689（一种有效的免疫刺激药）的轻松合成得到了证明。
• Synthesis of 1,4-Disubstituted Pyrazolo[3,4-d]pyrimidines from 4,6-Dichloropyrimidine-5-carboxaldehyde: Insights into Selectivity and Reactivity
  作者：Christie Morrill、Young-Choon Moon、Suresh Babu、Neil Almstead

  DOI：10.1055/s-0033-1338862

  日期：——

  Strategies for carrying out the reaction of 4,6-dichloropyrimidine-5-carboxaldehyde with both aromatic and aliphatic hydrazines to generate 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines in a selective, high-yielding, and operationally simple manner are presented. For aromatic hydrazines, the reaction is performed at a high temperature in the absence of an external base. For aliphatic hydrazines, the reaction proceeds at room temperature in the presence of an external base. The observed selectivity and reactivity trends are rationalized through consideration of the proposed reaction mechanism. The 1-substituted 4-chloropyrazolo[3,4-d]pyrimidine products serve as versatile synthetic intermediates, through further functionalization of the 4-chloride moiety, enabling the rapid generation of a structurally diverse array of 1,4-disubstituted pyrazolo[3,4-d]pyrimidines.
• Selective Synthesis of 1-Substituted 4-Chloropyrazolo[3,4-<i>d</i>]pyrimidines
  作者：Suresh Babu、Christie Morrill、Neil G. Almstead、Young-Choon Moon

  DOI：10.1021/ol4005382

  日期：2013.4.19

  Strategies for carrying out the reaction of 4,6-dichloropyrimidine-5-carboxaldehyde with various hydrazines to generate 1-substituted 4-chloropyrazolo[3,4-d]pyrimidines in a selective and high-yielding manner are presented. For aromatic hydrazines, the reaction is performed in the absence of an external base, which promotes exclusive hydrazone formation. The hydrazones subsequently cyclize at an elevated temperature to form the desired pyrazolo[3,4-d]pyrimidine products. For aliphatic hydrazines, the reaction sequence proceeds as a single step in the presence of an external base.
• US4100286A
  申请人：——

  公开号：US4100286A

  公开（公告）日：1978-07-11