2-amino-5-{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine | 171887-02-8

• 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: 2-amino-5-{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine
• 英文别名: N'-(2-amino-4,6-dichloropyrimidin-5-yl)-N,N-dimethylformamidine；2-Amino-4,6-dichloro-5-{[(dimethylamino)methylene]amino}pyrimidine；N'-(2-amino-4,6-dichloropyrimidin-5-yl)-N,N-dimethylmethanimidamide
• CAS: 171887-02-8
• 化学式: C₇H₉Cl₂N₅
• 分子量: 234.088
• InChiKey: FLSVUQSDOOPGNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-5-{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine 在 三乙胺 作用下， 以 phosphate buffer 、 乙醇 、 正丁醇 为溶剂， 反应 32.0h， 生成 阿巴卡韦
  参考文献：
  名称：

  An Efficient, Scalable Synthesis of the HIV Reverse Transcriptase Inhibitor Ziagen® (1592U89)

  摘要：

  Ziagen(R), (IS, cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol, was synthesized from (IS,4R)-azabicyclo[2.2.1]hept-5-en-3-one by efficient processes which bypass problematic steps in earlier routes. 2-Amino-4,6-dichloro-5-formamidopyrimidine is a key intermediate which makes possible an efficient construction of the purine from a chiral cyclopentenyl precursor.

  DOI：

  10.1080/15257770008033011
• 作为产物：
  描述：

  2,5-bis{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以95%的产率得到2-amino-5-{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine
  参考文献：
  名称：

  An Efficient, Scalable Synthesis of the HIV Reverse Transcriptase Inhibitor Ziagen® (1592U89)

  摘要：

  Ziagen(R), (IS, cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol, was synthesized from (IS,4R)-azabicyclo[2.2.1]hept-5-en-3-one by efficient processes which bypass problematic steps in earlier routes. 2-Amino-4,6-dichloro-5-formamidopyrimidine is a key intermediate which makes possible an efficient construction of the purine from a chiral cyclopentenyl precursor.

  DOI：

  10.1080/15257770008033011

文献信息

• [EN] METHOD FOR SYNTHESIZING DIVERSELY SUBSTITUTED PURINES<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE PURINES À SUBSTITUTIONS DIVERSES
  申请人：UNIV GRENOBLE ALPES

  公开号：WO2018203099A1

  公开（公告）日：2018-11-08

  The present invention relates to a method for synthesizing diversely substituted purines starting from a pyrimidine. Formula (I). The method comprises the formation of an amidine group on the pyrimidine by implementing a Vilsmeier type reagent, the functionalization of the pyrimidine with an amine and the cyclization to form the purine nucleus. Optional steps can also be performed in order to further functionalize the molecule. The invention also relates to new purines and new intermediate product.

  本发明涉及一种从嘧啶开始合成多样取代嘌呤的方法。公式（I）。该方法包括通过实施Vilsmeier型试剂在嘧啶上形成酰胺基团，用胺对嘧啶进行官能化，并进行环化以形成嘌呤核。还可以执行可选步骤以进一步官能化分子。该发明还涉及新的嘌呤和新的中间产物。
• A One-Pot Synthesis of Highly Functionalized Purines
  作者：Renaud Zelli、Waël Zeinyeh、Romain Haudecoeur、Julien Alliot、Benjamin Boucherle、Isabelle Callebaut、Jean-Luc Décout

  DOI：10.1021/acs.orglett.7b03209

  日期：2017.12.1

  Highly substituted purines were synthesized in good to high yields through a one-pot straightforward metal-free scalable method, using the Traube synthesis adapted to Vilsmeier-type reagents. From 5-amino-4-chloropyrimidines, new 9-aryl-substituted chloropurines and intermediates for peptide nucleic acid synthesis were prepared. Variant procedures allowing a rapid synthesis of ribonucleosides and 7-benzylpurine

  使用适合Vilsmeier型试剂的Traube合成，通过一锅简单，无金属的可扩展方法，可以高产量合成高取代的嘌呤。由5-氨基-4-氯嘧啶，制备新的9-芳基取代的氯嘌呤和用于肽核酸合成的中间体。还报道了允许从5-ami基-6-氨基嘧啶快速合成核糖核苷和7-苄基嘌呤的各种方法，以说明这种多功能工具箱的巨大潜力。该途径在核酸领域中对于直接和快速地获得各种新的8-烷基嘌呤核苷似乎是特别令人感兴趣的。
• Chloropvrimidine intermediates
  申请人：——

  公开号：US20020173649A1

  公开（公告）日：2002-11-21

  The present invention relates to certain novel pyrimidine intermediates and their salts, processes for their preparation and processes for their conversion to 9-substituted-2-aminopurines which are useful in medical therapy.

  本发明涉及某些新型嘧啶中间体及其盐，其制备方法和转化为9-取代基-2-氨基嘌呤的方法，这些化合物在医疗治疗中有用。
• 4,6-dichloropyrimidine and related compounds
  申请人：Lonza AG

  公开号：US05583226A1

  公开（公告）日：1996-12-10

  A novel pyrimidine derivative, N-(2-amino-4,6-dichloropyrimidine-5-yl)formamide for use, e.g., in the production of antiviral nucleotide derivatives, can be made by a process involving cyclyzing an aminomalonic ester with guanidine or its salt in the presence of a base to produce 2,5-diamino-4,6-dihydroxypyrimidine or its salt, chlorinating this product with a chlorinating agent in the presence of an amide to produce 4,6-dichloropyrimidine, and reacting the 4,6-dichlororpyrimidine with an aqueous solution of a carboxylic acid to produce the N-(2-amino-4,6-dichloropyrimidine-5-yl)formammide. Novel also are 4,6-dichloropyrimidine, 4,6-dichloro-N'-(dimethylaminomethylene)pyrimidine-2,5-diamine, 4,6-dichloro-N'-(piperidine-1-ylmethylene)pyrimidine-2,5-diamine, and a process for making 2,5-diamino-4,6-dichloropyrimidine.

  一种新的嘧啶衍生物N-(2-氨基-4,6-二氯嘧啶-5-基)甲酰胺，可用于制备抗病毒核苷衍生物，其制备过程包括在碱存在下，使氨基丙二酸酯与胍或其盐环化，生成2,5-二氨基-4,6-二羟基嘧啶或其盐，使用氯代试剂在酰胺存在下氯化该产物，生成4,6-二氯嘧啶，然后将4,6-二氯嘧啶与羧酸的水溶液反应，生成N-(2-氨基-4,6-二氯嘧啶-5-基)甲酰胺。此外，还涉及4,6-二氯嘧啶、4,6-二氯-N'-(二甲基氨基甲烯基)嘧啶-2,5-二胺、4,6-二氯-N'-(哌啶-1-基甲烯基)嘧啶-2,5-二胺和制备2,5-二氨基-4,6-二氯嘧啶的方法。
• Chloropyrimidine intermediates
  申请人：SmithKline Beecham Corporation

  公开号：US06448403B1

  公开（公告）日：2002-09-10

  A compound of formula (VI) A process for the preparation of a compound of formula (VI): comprising: reacting a compound of formula (III): with an amine of formula R3NH2.

  化合物公式为(VI)的化合物，制备方法包括：将化合物公式为(III)的化合物与公式为R3NH2的胺反应。