Ethyl 4-<2-(2,4-diaminopyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoate | 151864-73-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 4-<2-(2,4-diaminopyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoate
• 英文别名: ethyl 4-(2-(2,4-diaminopyrrolo[2,3-d]pyrimidin-5-yl)ethyl}benzoate；Ethyl 4-{2-(2,4-diaminopyrrolo[2,3-d]pyrimidin-5-yl)ethyl}benzoate；ethyl 4-[2-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoate
• CAS: 151864-73-2
• 化学式: C₁₇H₁₉N₅O₂
• 分子量: 325.37
• InChiKey: GRXFIDLCISVXKU-UHFFFAOYSA-N

物化性质

• 沸点：
  547.0±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 4-<2-(2,4-diaminopyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoate 生成 培美酸
  参考文献：
  名称：

  CA2084490A1

  摘要：

  公开号：
• 作为产物：
  描述：

  对乙氧基甲酰苯丙醛 在 三乙胺 、 3-ethylbenzothiazolium bromide 4 A molecular sieve 、 sodium ethanolate 、 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 96.0h， 生成 Ethyl 4-<2-(2,4-diaminopyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoate
  参考文献：
  名称：

  WO2008/89390

  摘要：

  公开号：

文献信息

• Process for the preparation of pyrrolo[2,3-d]pyrimidines
  申请人：The Trustees of Princeton University

  公开号：US05254687A1

  公开（公告）日：1993-10-19

  5-Substituted pyrrolo[2,3-d]pyrimidines are prepared from a nucleophile of the formula R.sup.2 -C(.dbd.NH)NH.sub.2 and a 2-amino-5-substituted-furan carrying a cyano or carboxy group in the 4-position. A typical example is the preparation of ethyl 4-(2-(2,4-diaminopyrrolo[2,3-d]pyrimidin-5-yl)ethyl}benzoate, an intermediate for the preparation of the known N-[4-2-(2,4-diaminopyrrolo[2,3-d]pyrimidin-5-yl)ethyl}benzoyl]-L-glutamic acid, by allowing guanidine and ethyl 4-[2-(2-amino-3-cyanofur-4-yl)ethyl]benzoate to react under mild conditions.

  5-取代吡咯并[2,3-d]嘧啶可由化学式为R.sup.2-C(.dbd.NH)NH.sub.2的亲核试剂和在4位带有氰基或羧基的2-氨基-5-取代呋喃反应制备而成。一个典型的例子是通过在温和的条件下让胍和乙酸乙酯4-[2-(2-氨基-3-氰基呋喃-4-基)乙基]苯酸酯反应制备出乙酸乙酯4-(2-(2,4-二氨基吡咯并[2,3-d]嘧啶-5-基)乙基)苯酸酯，这是制备已知的N-[4-2-(2,4-二氨基吡咯并[2,3-d]嘧啶-5-基)乙基}苯甲酰]-L-谷氨酸的中间体。
• [EN] PROCESS FOR THE PREPARATION OF PYRROLO[2,3-D]PYRIMIDINES<br/>[FR] PROCEDE DE PREPARATION DE PYRROLO[2,3-D]PYRIMIDINES
  申请人：UNIV PRINCETON

  公开号：WO2000011004A1

  公开（公告）日：2000-03-02

  4(3H)-X-7H-Pyrrolo[2,3-d]pyrimidines in which X is =O or =NH are prepared by (i) treating a 6-amino-4(3H)-X-pyrimidine with a unsubstituted or substituted 1-nitroalk-1-ene to yield a 6-amino-4(3H)-X-pyrimidine which is substituted in the 5-position by a 1-nitroalk-2-yl group; (ii) converting the 5-(1-nitroalk-2-yl)-6-amino-4(3H)-X-pyrimidine to the corresponding 5-(1-oxoalk-2-yl)-6-amino-4(3H)-X-pyrimidine; and (iii) removing the elements of water from the 5-(1-oxoalk-2-yl)-6-amino-4(3H)-X-pyrimidine to effect cyclization. A typical embodiment involves treating 2,6-diamino-4(3H)-pyrimidone with 1-nitro-4-(4-ethoxycarbonylphenyl)-I-butene to yield 1-nitro-2-(2,6-diamino 4(3H)-oxopyrimidin-5-yl)-4-(4-ethoxycarbonylphenyl)butane which is then treated sequentially with base and acid, without isolation of the intermediate aldehyde, to form 4-[2-(2-amino-4(3H)-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid, a valuable known chemical intermediate for the preparation of N-[4-2-(2-hydroxy-4-amino-7H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl}benzoyl]glutamic acid.

  本发明涉及一种制备4(3H)-X-7H-吡咯并[2,3-d]嘧啶的方法，其中X = O或= NH，包括以下步骤：(i)用非取代或取代的1-硝基烯烃处理6-氨基-4(3H)-X-嘧啶，得到在5-位上被1-硝基烷基取代的6-氨基-4(3H)-X-嘧啶；(ii)将5-(1-硝基烷基-2-基)-6-氨基-4(3H)-X-嘧啶转化为相应的5-(1-氧代烷基-2-基)-6-氨基-4(3H)-X-嘧啶；(iii)从5-(1-氧代烷基-2-基)-6-氨基-4(3H)-X-嘧啶中除去水分以进行环化。典型实施例包括用1-硝基-4-(4-乙氧羰基苯基)-1-丁烯处理2,6-二氨基-4(3H)-嘧啶，得到1-硝基-2-(2,6-二氨基4(3H)-氧代嘧啶-5-基)-4-(4-乙氧羰基苯基)丁烷，然后依次用碱和酸处理而不分离中间体醛，形成4-[2-(2-氨基-4(3H)-氧代-7H-吡咯并[2,3-d]嘧啶-5-基)乙基]苯甲酸，这是制备N-[4-2-(2-羟基-4-氨基-7H-吡咯并[2,3-d]-嘧啶-5-基)乙基}苯甲酰]谷氨酸的有价值的已知化学中间体。
• A One-Step Ring Transformation/Ring Annulation Approach to Pyrrolo[2,3-d]pyrimidines. A New Synthesis of the Potent Dihydrofolate Reductase Inhibitor TNP-351
  作者：Edward C. Taylor、Hemantkumar H. Patel、Jong-Gab Jun

  DOI：10.1021/jo00126a017

  日期：1995.10

  Condensation of amidines with 2-amino-3-cyanofurans gives 2-substituted-4-aminopyrrolo[2,3-d]-pyrimidines by a ring-opening, ring-recyclization sequence of reactions through which the starting furan 2-amino nitrogen becomes the pyrrole nitrogen of the final product and one of the amidine nitrogens becomes N-1 of the fused pyrimidine ring. 2,4-Diamino-5-[2-(4-carbethoxyphenyl)ethyl]- pyrrolo[2,3-d]pyrimidine, a key intermediate in the synthesis of the DHFR inhibitor TNP-351, has been prepared in one step by reaction of ethyl 4-[2-(2-amino-3-cyanofuran-4-yl)ethyl]be with guanidine.
• CA2084490A1
  申请人：——

  公开号：——

  公开（公告）日：——
• PROCESS FOR THE PREPARATION OF PYRROLO[2,3-D]PYRIMIDINES
  申请人：The Trustees of Princeton University

  公开号：EP1105396A1

  公开（公告）日：2001-06-13