2-氨基吡啶-D6 | 203784-57-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-氨基吡啶-D6
• 中文别名: 2-氨基吡啶
• 英文名称: [G-2H]-2-aminopyridine
• 英文别名: 2-aminopyridine-d6；N,N,3,4,5,6-hexadeuteriopyridin-2-amine
• CAS: 203784-57-0
• 化学式: C₅H₆N₂
• 分子量: 100.068
• InChiKey: ICSNLGPSRYBMBD-UDDMDDBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 海关编码：
  2942000000

反应信息

• 作为反应物：
  描述：

  2-氨基吡啶-D6 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 、 氢溴酸 、 溴 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 5-Bromo-2-[5-(5-bromo-3,4,6-trideuteriopyridin-2-yl)furan-2-yl]-3,4,6-trideuteriopyridine
  参考文献：
  名称：

  Synthesis of deuterium and15N-labelled 2,5-Bis[5-amidino-2-pyridyl]furan and 2,5-Bis[5-(methoxyamidino)-2-pyridyl]furan

  摘要：

  2,5-双[5-脒基-2-吡啶基]呋喃-d2/15N2 的乙酸盐（4）是由 2,5-双[5-氰基-2-吡啶基]呋喃-d2（2）通过双-O-乙酰氧基脒肟加氢合成的。化合物 2 是通过 6-氯烟腈与 2,5-双[三正丁基锡]-呋喃-d2（1）的 Stille 偶联反应得到的。2,5-双[5-脒基-2-吡啶基]呋喃-d6 (10) 是由 2,5-双[5-氰基-2-吡啶基]呋喃-d6 (9) 与双(三甲基硅烷基)酰胺锂直接反应，然后用乙醇盐酸进行脱保护而合成的。在 DMF 溶液中，以 LiOH 为碱，用二甲基硫酸酯-d0 或二甲基硫酸酯-d6 直接甲基化各自的二脒肟，制备了 15N 和/或氘标记的甲氧基酰胺 5a-d2/15N2、5b-d8、12、14-d6，收率良好。Copyright © 2006 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.1111
• 作为产物：
  描述：

  2-氨基吡啶 在 palladium on activated charcoal 氢气 、 重水 作用下， 反应 24.0h， 生成 2-氨基吡啶-D6
  参考文献：
  名称：

  General method of obtaining deuterium-labeled heterocyclic compounds using neutral D2O with heterogeneous Pd/C

  摘要：

  A protocol of a versatile H-D exchange reaction of heterocyclic compounds catalyzed by heterogeneous Pd/C in D2O is described. The reaction of various nitrogen-containing heterocycles with 10% Pd/C (10 wt % of the substrate) under hydrogen atmosphere in D2O as a deuterium source at 110-180 degrees C for 24 h afforded the corresponding deuterated compounds with satisfactory efficiency of deuteration in moderate to excellent isolated yields. Furthermore, the Pd/C-H-2-D2O system can be extended to the direct deuteration of biologically active compounds such as sulfamethazine, which is used as a synthetic antibacterial drug for fat stocks and would be applied as a general method for the preparation of the standard materials for the analysis of residual chemicals in foods and so on. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.088

文献信息

• General method of obtaining deuterium-labeled heterocyclic compounds using neutral D2O with heterogeneous Pd/C
  作者：Hiroyoshi Esaki、Nobuhiro Ito、Shino Sakai、Tomohiro Maegawa、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1016/j.tet.2006.08.088

  日期：2006.11

  A protocol of a versatile H-D exchange reaction of heterocyclic compounds catalyzed by heterogeneous Pd/C in D2O is described. The reaction of various nitrogen-containing heterocycles with 10% Pd/C (10 wt % of the substrate) under hydrogen atmosphere in D2O as a deuterium source at 110-180 degrees C for 24 h afforded the corresponding deuterated compounds with satisfactory efficiency of deuteration in moderate to excellent isolated yields. Furthermore, the Pd/C-H-2-D2O system can be extended to the direct deuteration of biologically active compounds such as sulfamethazine, which is used as a synthetic antibacterial drug for fat stocks and would be applied as a general method for the preparation of the standard materials for the analysis of residual chemicals in foods and so on. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of deuterium and15N-labelled 2,5-Bis[5-amidino-2-pyridyl]furan and 2,5-Bis[5-(methoxyamidino)-2-pyridyl]furan
  作者：Mohamed A. Ismail、David W. Boykin

  DOI：10.1002/jlcr.1111

  日期：2006.10.15

  The acetate salt of 2,5-bis[5-amidino-2-pyridyl]furan-d2/15N2 (4) was synthesized from 2,5-bis[5-cyano-2-pyridyl]furan-d2 (2), through the bis-O-acetoxyamidoxime followed by hydrogenation. Compound 2 was obtained via a Stille coupling reaction of 6-chloronicotinonitrile with 2,5-bis[tri-n-butyltin]-furan-d2 (1). 2,5-bis[5-amidino-2-pyridyl)furan-d6 (10) was synthesized from 2,5-bis[5-cyano-2-pyridyl)furan-d6 (9) via a direct reaction with lithium bis(trimethylsilyl)amide, followed by deprotection with ethanolic HCl. 15N and/or deuterium-labelled methoxy-amidines 5a-d2/15N2, 5b-d8, 12, 14-d6 were prepared in good yield via direct methylation of their respective diamidoximes with either dimethylsulfate-d0 or dimethylsulfate-d6 in DMF solution and using LiOH as a base. Copyright © 2006 John Wiley & Sons, Ltd.

  2,5-双[5-脒基-2-吡啶基]呋喃-d2/15N2 的乙酸盐（4）是由 2,5-双[5-氰基-2-吡啶基]呋喃-d2（2）通过双-O-乙酰氧基脒肟加氢合成的。化合物 2 是通过 6-氯烟腈与 2,5-双[三正丁基锡]-呋喃-d2（1）的 Stille 偶联反应得到的。2,5-双[5-脒基-2-吡啶基]呋喃-d6 (10) 是由 2,5-双[5-氰基-2-吡啶基]呋喃-d6 (9) 与双(三甲基硅烷基)酰胺锂直接反应，然后用乙醇盐酸进行脱保护而合成的。在 DMF 溶液中，以 LiOH 为碱，用二甲基硫酸酯-d0 或二甲基硫酸酯-d6 直接甲基化各自的二脒肟，制备了 15N 和/或氘标记的甲氧基酰胺 5a-d2/15N2、5b-d8、12、14-d6，收率良好。Copyright © 2006 John Wiley & Sons, Ltd. All Rights Reserved.