4,6-dichloro-2-(dimethylamino)-5-(methylthio)pyrimidine | 55416-84-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,6-dichloro-2-(dimethylamino)-5-(methylthio)pyrimidine
• 英文别名: (4,6-dichloro-5-methylsulfanyl-pyrimidin-2-yl)-dimethyl-amine；2-Dimethylamino-4,6-dichloro-5-methylthio-pyrimidine；4,6-dichloro-N,N-dimethyl-5-methylsulfanylpyrimidin-2-amine
• CAS: 55416-84-7
• 化学式: C₇H₉Cl₂N₃S
• 分子量: 238.141
• InChiKey: SUARBYKFCNHIFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 4,6-dichloro-2-(dimethylamino)-5-(methylthio)pyrimidine 在 三乙胺 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 6-chloro-2-(dimethylamino)-4-(N-methylpiperazino)-5-(methylthio)pyrimidine
  参考文献：
  名称：

  2-氨基-6-氯-4-（N-甲基哌嗪子基）嘧啶类药物，螺哌啶醇结合抑制剂。

  摘要：

  合成了一系列30个6-氯-2,4-二氨基嘧啶，并作为[3H]螺哌啶醇结合的抑制剂进行了体外测试。对多巴胺受体的亲和力表明与2位上带有NH2或NHR1基团作为取代基的6-氯-4-（N-甲基-哌嗪）嘧啶结构有关，但前提是R1不是α支链烷基组。5位的取代基的性质对于亲和力也很重要。2-（苄氨基）-6-氯-4-（N-甲基哌嗪子基）-5-（甲硫基）嘧啶（22）是该系列中最活跃的成员。通过X射线衍射和PCILO计算分析了三种化合物的分子结构。

  DOI：

  10.1021/jm00354a014

文献信息

• 5-Methylthio-pyrimidine vasodilators
  申请人：Produits Chimiques Ugine Kuhlmann

  公开号：US03968214A1

  公开（公告）日：1976-07-06

  The compounds of the formula: ##SPC1## In which Y represents a chlorine atom or an alkoxy, dialkylaminoalkoxy, pyridylalkoxy group, R.sub.1 and R.sub.2 are identical or different substituents and represent alkyl or alkoxycarbonylalkyl groups, substituted or unsubstituted phenyl groups or form together with the nitrogen atom to which they are attached, a heterocyclic ring which may contain another hetero-atom, R.sub.3 and R.sub.4 are identical or different substituents and represent alkyl groups or form, together with the nitrogen atom to which they are attached, a heterocyclic ring which may contain another hetero-atom; process for their preparation; medicaments comprising such compounds or salts thereof, and their use in the treatment of human beings. The present invention relates to new pyrimidines, to their use as medicaments on account of their spasmolytic, coronary dilator and hypoglycemiant properties and to their preparation. These compounds, derived from 5-methylthio-pyrimidine, may be represented by the general formula: ##SPC2## In which Y represents a chlorine atom or an alkoxy, dialkylaminoalkoxy or pyridylalkoxy group, the alkoxy and alkyl groups preferably containing 1 to 4 carbon atoms, R.sub.1 and R.sub.2 are identical or different substituents and represent alkyl, alkoxycarbonylalkyl, substituted or unsubstituted phenyl or benzyl groups or form, together with the nitrogen atom to which they are attached, a heterocyclic ring which may contain another hetero-atom, the alkyl and alkoxy groups preferably containing 1 to 4 carbon atoms, R.sub.3 and R.sub.4 are identical or different substituents and represent alkyl groups preferably containing 1 to 4 carbon atoms or form, together with the nitrogen atom to which they are attached, a heterocyclic ring which may possibly contain another hetero-atom. Substituents of the phenyl group may be for example halogen atoms or alkyl, alkoxy or trihalomethyl groups. The compounds of formula (I) may be prepared for example by reacting a compound of the formula: ##SPC3## In which R.sub.1 and R.sub.2 have the same significance as above, with an ethylenediamine of the formula: ##EQU1## in which R.sub.3 and R.sub.4 have the same significance as above, and possibly replacing the remaining chlorine atom by an alkoxy, dialkylamino-alkoxy or pyridylalkoxy group. The reaction with the compound of formula (III) is preferably effected in a solvent, in the presence of an acid-absorbing agent, at a temperature between 20.degree.C. and 100.degree.C. The substitution of the remaining chlorine atom may be effected for example by the action of an alcoholate of an alkali metal or by the action of an excess of the corresponding alcohol and caustic potash at the refluxing temperature.

  该公式的化合物：##SPC1## 其中Y表示氯原子或烷氧基，二烷基氨基烷氧基，吡啶基烷氧基，R.sub.1和R.sub.2是相同或不同的取代基，表示烷基或烷氧基羧基烷基，取代或未取代的苯基或与它们所附着的氮原子一起形成可能包含另一个杂原子的杂环，R.sub.3和R.sub.4是相同或不同的取代基，表示烷基或与它们所附着的氮原子一起形成可能包含另一个杂原子的杂环；制备这些化合物的过程；包括这种化合物或其盐的药物以及它们在治疗人类方面的用途。本发明涉及新的嘧啶类化合物，由于它们的平滑肌松弛、冠状动脉扩张和降血糖特性而用作药物，以及它们的制备。这些化合物由5-甲基硫代嘧啶衍生而来，可以用下列通式表示：##SPC2## 其中Y表示氯原子或烷氧基，二烷基氨基烷氧基或吡啶基烷氧基，烷氧基和烷基群体最好含有1至4个碳原子，R.sub.1和R.sub.2是相同或不同的取代基，表示烷基，烷氧基羧基烷基，取代或未取代的苯基或苄基，或与它们所附着的氮原子一起形成可能包含另一个杂原子的杂环，烷基和烷氧基群体最好含有1至4个碳原子，R.sub.3和R.sub.4是相同或不同的取代基，表示最好含有1至4个碳原子的烷基或与它们所附着的氮原子一起形成可能包含另一个杂原子的杂环。苯基的取代基可以是卤原子或烷基，烷氧基或三卤甲基基团等。公式（I）的化合物可以通过将具有以下式的化合物：##SPC3## 其中R.sub.1和R.sub.2具有上述相同的意义，与具有以下式的乙二胺反应而制备：##EQU1## 其中R.sub.3和R.sub.4具有上述相同的意义，并可能用烷氧基，二烷基氨基烷氧基或吡啶基烷氧基群体代替剩余的氯原子。与公式（III）的化合物的反应最好在溶剂中，在酸吸收剂的存在下，在20℃至100℃的温度下进行。剩余氯原子的取代可以通过碱金属醇盐的作用或通过相应醇的过量作用和氢氧化钾在回流温度下的作用来实现。
• GUEREMY, C.;AUDIAU, F.;UZAN, A.;LE, FUR, G.;LEGER, J. -M.;CARPY, A., J. MED. CHEM., 1982, 25, N 12, 1459-1465
  作者：GUEREMY, C.、AUDIAU, F.、UZAN, A.、LE, FUR, G.、LEGER, J. -M.、CARPY, A.

  DOI：——

  日期：——
• US3968214A
  申请人：——

  公开号：US3968214A

  公开（公告）日：1976-07-06