4,6-dichloro-2-[2]naphthyl-5-nitro-pyrimidine | 873398-63-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,6-dichloro-2-[2]naphthyl-5-nitro-pyrimidine
• 英文别名: 4,6-Dichlor-2-[2]naphthyl-5-nitro-pyrimidin；4,6-Dichloro-2-naphthalen-2-yl-5-nitropyrimidine
• CAS: 873398-63-1
• 化学式: C₁₄H₇Cl₂N₃O₂
• 分子量: 320.134
• InChiKey: VYGICCBDNZCVAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙烯亚胺 、 4,6-dichloro-2-[2]naphthyl-5-nitro-pyrimidine 生成 4,6-bis-aziridin-1-yl-2-[2]naphthyl-5-nitro-pyrimidine
  参考文献：
  名称：

  Consensus strategy in suspected pulmonary embolism

  摘要：

  DOI：

  10.1093/qjmed/93.9.639
• 作为产物：
  描述：

  2-[2]naphthyl-1H-pyrimidine-4,6-dione 在 硝酸 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 生成 4,6-dichloro-2-[2]naphthyl-5-nitro-pyrimidine
  参考文献：
  名称：

  Consensus strategy in suspected pulmonary embolism

  摘要：

  DOI：

  10.1093/qjmed/93.9.639

文献信息

• 2-4-diethyleneimino pyrimidines and process of preparing same
  申请人：ICI LTD

  公开号：US02675386A1

  公开（公告）日：1954-04-13

  The invention comprises pyrimidine derivatives bearing in the p 2-, 4- or 6-positions two ethyleneimino substituents and optionally bearing one or more further non-acidic substituents; the preparation thereof by reacting a pyrimidine derivative, bearing in the 2-, 4- or 6-positions at least two halogen substituents and optionally bearing one or more further non-acidic substituents, with ethyleneimine (preferably in a liquid medium, e.g. water or benzene, and in the presence of an acid-binding agent, e.g. an alkali metal carbonate or triethylamine) or with an alkali metal (preferably lithium) derivative of ethyleneimine; the reaction of such of the products as contain a residual halogen atom with an alkali metal alkoxide; and the reduction with hydrogen of such of the products as contain a nitro group. The products are cytotoxic and possess tumour-inhibiting properties. Examples describe the use of the following starting materials: (1) and (2) 5-nitro-4 : 6-dichloropyrimidine and its 2-methyl derivative; (3) 5-nitro-2 : 4-dichloropyrimidine; (4) 2 : 4 : 6-trichloropyrimidine (yielding 6 - chloro - 2 : 4 - bis - ethyleneiminopyrimidine); (5) 2-phenyl-5-nitro-4 : 6-dichloropyrimidine; (6) 2-phenyl- and 2-b -naphthyl-4 : 6-dichloropyrimidine; (7) 5-phenyl-2 : 4 : 6-trichloropyrimidine (yielding 5 - phenyl - 6-chloro - 2 : 4 - bis - ethyleneiminopyrimidine); (10) 2 - b - naphthyl - 5 - nitro - 4 : 6 - dichloropyrimidine; (11) 2-dimethylamino-4 : 6-dichloro-5-nitropyrimidine. In further examples: (8) the product of (4) is warmed with a solution of sodium in methyl, ethyl or isopropyl alcohol to produce 6-methoxy-, 6-ethoxy, or 6-isopropoxy - 2 : 4 - bis - ethyleneimino - pyrimidine; (9) 5-nitro-2-phenyl-4 : 6-bis-ethylene-imino-pyrimidine is shaken with hydrogen and Raney nickel in methyl alcohol and benzene to from the corresponding 5-amino compound. 5 - Nitro - 4 : 6 - dichloropyrimidine and its 2-phenyl, 2-b -naphthyl and 2-dimethylamino derivatives are obtainable by nitration of, respectively, 4 : 6 - dihydroxypyrimidine (obtained by condensation of formamidine with diethyl malonate), its 2-phenyl derivative, its 2-b -naphthyl derivative (obtained by condensation of b -naphthamidine with diethyl malonate in the presence of sodium ethoxide) and its 2-dimethylamino derivative (obtained by condensation of dimethylguanidine with diethyl malonate), and treatment of the products with phosphorus oxychloride in the presence of dimethylaniline. 5 - Nitro - 2 : 4 - dichloropyrimidine is obtainable similarly from uracil. 2 - Phenyl - 4 : 6 - dichloropyrimidine and 5 - phenyl - 2 : 4 : 6 - trichloropyrimidine are obtainable by the treatment of 2-phenyl-4 : 6-dihydroxypyrimidine and 5-phenylbarbituric acid respectively with phosphorus oxychloride.

  该发明涉及在嘧啶衍生物中的p 2-、4-或6-位置带有两个乙烯亚胺取代基，并且可选择地带有一个或多个进一步的非酸性取代基；通过将在2-、4-或6-位置至少带有两个卤素取代基并且可选择地带有一个或多个进一步的非酸性取代基的嘧啶衍生物与乙烯亚胺（最好在液体介质中，例如水或苯，并在碱性剂的存在下，例如碱金属碳酸盐或三乙胺）或与乙烯亚胺的碱金属（最好是锂）衍生物反应来制备；将含有残留卤素原子的产品与碱金属烷氧化物反应；将含有硝基的产品用氢还原。这些产品具有细胞毒性并具有抑制肿瘤的性质。示例描述了以下起始材料的用途：（1）和（2）5-硝基-4：6-二氯嘧啶及其2-甲基衍生物；（3）5-硝基-2：4-二氯嘧啶；（4）2：4：6-三氯嘧啶（生成6-氯-2：4-双-乙烯亚胺嘧啶）；（5）2-苯基-5-硝基-4：6-二氯嘧啶；（6）2-苯基和2-β-萘基-4：6-二氯嘧啶；（7）5-苯基-2：4：6-三氯嘧啶（生成5-苯基-6-氯-2：4-双-乙烯亚胺嘧啶）；（10）2-β-萘基-5-硝基-4：6-二氯嘧啶；（11）2-二甲基氨基-4：6-二氯-5-硝基嘧啶。在进一步的示例中：（8）（4）的产物与甲醇、乙醇或异丙醇中的钠溶液加热，产生6-甲氧基、6-乙氧基或6-异丙氧基-2：4-双-乙烯亚胺-嘧啶；（9）5-硝基-2-苯基-4：6-双-乙烯亚胺嘧啶与氢气和Raney镍在甲醇和苯中振荡，形成相应的5-氨基化合物。5-硝基-4：6-二氯嘧啶及其2-苯基、2-β-萘基和2-二甲基氨基衍生物可以通过对4：6-二羟基嘧啶（通过甲酰胺与二乙基丙二酸酯缩合得到）、其2-苯基衍生物、其2-β-萘基衍生物（通过β-萘胺与二乙基丙二酸酯在存在乙醇钠的情况下缩合得到）和其2-二甲基氨基衍生物（通过二甲基胍与二乙基丙二酸酯缩合得到），然后在二甲苯胺存在下用氯化亚磷处理得到。5-硝基-2：4-二氯嘧啶可以类似地从尿嘧啶中获得。2-苯基-4：6-二氯嘧啶和5-苯基-2：4：6-三氯嘧啶可以通过用氯化亚磷处理2-苯基-4：6-二羟基嘧啶和5-苯基咪唑烷酸分别得到。