(R)-3-(5-chloropyrimidin-2-yloxy)pyrrolidine | 927691-30-3

• 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: (R)-3-(5-chloropyrimidin-2-yloxy)pyrrolidine
• 英文别名: 5-chloro-2-[(3R)-pyrrolidin-3-yl]oxypyrimidine
• CAS: 927691-30-3
• 化学式: C₈H₁₀ClN₃O
• 分子量: 199.64
• InChiKey: LAGRBRPKSSCZIM-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-(5-chloropyrimidin-2-yloxy)pyrrolidine 、 4-氯-6,7-二甲氧基喹唑啉 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以72%的产率得到(R)-4-[3-(5-chloropyrimidin-2-yloxy)pyrrolidin-1-yl]-6,7-dimethoxyquinazoline
  参考文献：
  名称：

  Discovery of a Series of 6,7-Dimethoxy-4-pyrrolidylquinazoline PDE10A Inhibitors

  摘要：

  A papaverine based pharmacophore model for PDE10A inhibition was generated via SBDD and used to design a library of 4-amino-6,7-dimethoxyquinazolines. From this library emerged an aryl ether pyrrolidyl 6,7-dimethoxyquinazoline series that became the focal point for additional modeling, X-ray, and synthetic efforts toward increasing PDE10A inhibitory potency and selectivity versus PDE3A/B. These efforts culminated in the discovery of 29, a potent and selective brain penetrable inhibitor of PDE10A.

  DOI：

  10.1021/jm060653b
• 作为产物：
  描述：

  (R)-3-(5-chloropyrimidin-2-yloxy)pyrrolidine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以0.075 g的产率得到(R)-3-(5-chloropyrimidin-2-yloxy)pyrrolidine
  参考文献：
  名称：

  Discovery of a Series of 6,7-Dimethoxy-4-pyrrolidylquinazoline PDE10A Inhibitors

  摘要：

  A papaverine based pharmacophore model for PDE10A inhibition was generated via SBDD and used to design a library of 4-amino-6,7-dimethoxyquinazolines. From this library emerged an aryl ether pyrrolidyl 6,7-dimethoxyquinazoline series that became the focal point for additional modeling, X-ray, and synthetic efforts toward increasing PDE10A inhibitory potency and selectivity versus PDE3A/B. These efforts culminated in the discovery of 29, a potent and selective brain penetrable inhibitor of PDE10A.

  DOI：

  10.1021/jm060653b

文献信息

• Discovery of a Series of 6,7-Dimethoxy-4-pyrrolidylquinazoline PDE10A Inhibitors
  作者：Thomas A. Chappie、John M. Humphrey、Martin P. Allen、Kimberly G. Estep、Carol B. Fox、Lorraine A. Lebel、Spiros Liras、Eric S. Marr、Frank S. Menniti、Jayvardhan Pandit、Christopher J. Schmidt、Meihua Tu、Robert D. Williams、Feng V. Yang

  DOI：10.1021/jm060653b

  日期：2007.1.1

  A papaverine based pharmacophore model for PDE10A inhibition was generated via SBDD and used to design a library of 4-amino-6,7-dimethoxyquinazolines. From this library emerged an aryl ether pyrrolidyl 6,7-dimethoxyquinazoline series that became the focal point for additional modeling, X-ray, and synthetic efforts toward increasing PDE10A inhibitory potency and selectivity versus PDE3A/B. These efforts culminated in the discovery of 29, a potent and selective brain penetrable inhibitor of PDE10A.