2-Amino-6-chloro-9-(2,2-dicarboethoxycyclopropyl)-purine | 134470-58-9

• 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: 2-Amino-6-chloro-9-(2,2-dicarboethoxycyclopropyl)-purine
• 英文别名: Diethyl 2-(2-amino-6-chloropurin-9-yl)cyclopropane-1,1-dicarboxylate
• CAS: 134470-58-9
• 化学式: C₁₄H₁₆ClN₅O₄
• 分子量: 353.765
• InChiKey: GTWUNQJLNRNZSW-UHFFFAOYSA-N

物化性质

• 沸点：
  540.1±60.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-Amino-6-chloro-9-(2,2-dicarboethoxycyclopropyl)-purine 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以74%的产率得到diethyl 2-<2-(2-aminopurin-9-yl)ethyl>malonate
  参考文献：
  名称：

  Regiospecific Michael additions with 2-aminopurines

  摘要：

  N-9 alkylated materials are the sole products obtained from extended reaction of 2-aminopurines (potential guanine precursors) with Michael acceptors. This was used as the basis for a highly regioselective synthesis of famciclovir. the oral form of the anti-herpesvirus agent penciclovir.

  DOI：

  10.1016/s0040-4039(00)61326-6
• 作为产物：
  描述：

  diethyl-2-(2-chloroethylidene)malonte 、 2-氨基-6-氯嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-Amino-6-chloro-9-(2,2-dicarboethoxycyclopropyl)-purine 、 2-(2-Amino-6-chloro-purin-7-yl)-cyclopropane-1,1-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Regiospecific Michael additions with 2-aminopurines

  摘要：

  N-9 alkylated materials are the sole products obtained from extended reaction of 2-aminopurines (potential guanine precursors) with Michael acceptors. This was used as the basis for a highly regioselective synthesis of famciclovir. the oral form of the anti-herpesvirus agent penciclovir.

  DOI：

  10.1016/s0040-4039(00)61326-6

文献信息

• Process for the preparation of purine compounds
  申请人：Beecham Group p.l.c.

  公开号：EP0420559A2

  公开（公告）日：1991-04-03

  A process for the preparation of a compound of formula (A): wherein X is hydrogen, hydroxy, chloro, C₁₋₆ alkoxy or phenyl C₁₋₆ alkoxy and Ra and Rb are hydrogen, including acyl and phosphate derivatives thereof; which process comprises: i) the preparation of a compound of formula (I): wherein R₁ is C₁₋₆ alkyl, or phenyl C₁₋₆ alkyl in which the phenyl group is optionally substituted; R₂ is hydrogen, hydroxy, chlorine, C₁₋₆ alkoxy, phenyl C₁₋₆ alkoxy or amino; and R₃ is halogen, C₁₋₆ alkylthio, C₁₋₆ alkylsulphonyl, azido, an amino group or a protected amino group, which process comprises the reaction of a compound of formula (II): with a compound of formula (VII): wherein Q is a leaving group, J is hydrogen or halo and R₁ is as hereinbefore defined; to give a compound of formula (VIII): followed by reduction of the compound of formula (VIII) to give a compound of formula (I) as hereinbefore defined; and, as necessary or desired, interconverting variables R₁, R₂ and R₃ to further values of R₁, R₂ and R₃; (ii) the conversion of the resulting compound of formula (I) to a compound of formula (A) by converting variable R₃, when other than amino, to amino, reducing the ester groups CO₂R₁ to CH₂OH and optionally forming acyl or phosphate derivatives thereof, and as necessary or desired converting variable R₂ in the compound of formula (I) to variable X in the compound of formula (A).

  一种制备式（A）化合物的工艺： 其中 X 是氢、羟基、氯、C₁₋₆烷氧基或苯基 C₁₋₆烷氧基，Ra 和 Rb 是氢，包括其酰基和磷酸衍生物；该工艺包括： i) 制备式 (I) 的化合物： 其中 R₁ 是 C₁₋₆ 烷基，或苯基 C₁₋₆ 烷基，其中苯基任选被取代；R₂ 是氢、羟基、氯、C₁₋₆ 烷氧基、苯基 C₁₋₆ 烷氧基或氨基；R₃是卤素、C₁₋₆烷硫基、C₁₋₆烷基磺酰基、叠氮基、氨基或受保护的氨基： 与式(VII)化合物反应： 其中 Q 为离去基团，J 为氢或卤代，R₁ 如前定义；得到式（VIII）化合物： 然后还原式 (VIII) 化合物，得到如前定义的式 (I) 化合物；并在必要或需要时，将变量 R₁、R₂ 和 R₃ 进一步转化为 R₁、R₂ 和 R₃ 的值； (ii) 通过将非氨基的变量 R₃ 转化为氨基，将酯基 CO₂R₁ 还原为 CH₂OH，并选择性地形成酰基或磷酸衍生物，以及根据需要将 式(I)化合物中的变量 R₂ 转化为式(A)化合物中的变量 X，将所得式(I)化合物转化为式(A)化合物。
• US5220024A
  申请人：——

  公开号：US5220024A

  公开（公告）日：1993-06-15
• Regiospecific Michael additions with 2-aminopurines
  作者：Graham R. Geen、Peter M. Kincey、Bernadette M. Choudary

  DOI：10.1016/s0040-4039(00)61326-6

  日期：1992.8

  N-9 alkylated materials are the sole products obtained from extended reaction of 2-aminopurines (potential guanine precursors) with Michael acceptors. This was used as the basis for a highly regioselective synthesis of famciclovir. the oral form of the anti-herpesvirus agent penciclovir.