2-(2,6-dichloro-4-pyridyl)-5-ethyl-6-methyl-3-(prop-2-ynyl)-4(3H)-pyrimidinone

• 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-(2,6-dichloro-4-pyridyl)-5-ethyl-6-methyl-3-(prop-2-ynyl)-4(3H)-pyrimidinone
• 英文别名: 2-(2,6-dichloro-pyridin-4-yl)-5-ethyl-6-methyl-3-propargyl-4(3H)-pyrimidinone；2-(2,6-dichloro-4-pyridyl)-5-ethyl-6-methyl-3-propargyl-4(3H)-pyrimidinone；2-(2,6-dichloropyridin-4-yl)-5-ethyl-6-methyl-3-prop-2-ynylpyrimidin-4-one
• 化学式: C₁₅H₁₃Cl₂N₃O
• 分子量: 322.194
• InChiKey: XWDHGWRKIXKZRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 2-(2,6-dichloropyridin-4-yl)-6-oxo-4-(phenylsulfanylmethyl)-4,5-dihydro-1H-pyrimidine-5-carboxylate 在 吡啶 、 potassium tert-butylate 、 sodium hydride 、 间氯过氧苯甲酸 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2,6-dichloro-4-pyridyl)-5-ethyl-6-methyl-3-(prop-2-ynyl)-4(3H)-pyrimidinone
  参考文献：
  名称：

  2-（2,6-二氯-4-吡啶基）-3-炔丙基-5-乙基-6-甲基-4（3H）-嘧啶酮的合成，一种有前途的新型除草剂

  摘要：

  报道了一种新颖的有希望的新型除草剂2-（2,6-二氯-4-吡啶基）-3-炔丙基-5-乙基-6-甲基-4（3 ）-嘧啶酮的合成方法（12）。区域选择性碳，然后进行氮，中间二价阴离子的二烷基化，以及（2）串联的“一锅”反应序列，涉及σ型亚砜消除，氯化锂诱导的甲氧基羰基脱甲基化，脱羧和异构化/芳构化。

  DOI：

  10.1016/s0040-4039(97)00946-5

文献信息

• Improved process for pyrimidinone compounds
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0812832A1

  公开（公告）日：1997-12-17

  This invention relates to a process for the preparation of pyrimidinone compounds of the formula wherein Ar is an optionally substituted aryl or heteroaromatic moiety, R3 is an optionally substituted alkyl, alkenyl, alkynyl, (C1-C6)alkoxy (C2-C6)alkyl or silyl (C3-C6)alkynyl, R5 is a hydrogen atom, halo, cyano or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy or alkylthio, and R6 is a hydrogen atom, cyano, or an optionally substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl or heteroaryl. The process comprises reaction of an amidine and a malonic acid derivative to give a hydroxypyrimidinone followed by conversion of the resulting hydroxypyrimidinone to a sulfonyloxypyrimidinone followed by reaction of the resulting sulfonyloxypyrimidinone with an organometallic reagent to give the desired pyrimidinone. The hydroxypyrimidinones, wherein R6 is hydroxy and sulfonyloxypyrimidinones wherein R6 is a substituted sulfonyloxy moiety, are themselves new and useful intermediates in the preparation of the desired pyrimidinones.

  这项发明涉及一种用于制备公式为的吡啶酮化合物的工艺 其中 Ar是可选地取代的芳香族或杂芳基部分， R3是可选地取代的烷基、烯基、炔基、(C1-C6)alkoxy (C2-C6)alkyl或硅基(C3-C6)炔基， R5是氢原子、卤素、氰基或可选地取代的烷基、烯基、炔基、烷氧基或烷硫基，和 R6是氢原子、氰基，或可选地取代的烷基、环烷基、烯基、炔基、芳香族、芳烷基或杂芳基。 该工艺包括将酰胺与马来酸衍生物反应以给出羟基吡啶酮，然后将所得羟基吡啶酮转化为磺酰氧基吡啶酮，然后将所得磺酰氧基吡啶酮与有机金属试剂反应以得到所需的吡啶酮。 其中R6是羟基的羟基吡啶酮和其中R6是取代磺酰氧基基团的磺酰氧基吡啶酮本身就是用于制备所需吡啶酮的新颖有用的中间体。
• Synthesis of herbicidal 3-substituted-4(3<i>H</i>)-pyrimidinones under high pressure
  作者：Artur Jezewski、Janusz Jurczak、Zev Lidert、Colin M. Tice

  DOI：10.1002/jhet.5570380316

  日期：2001.5

  a pyrimidinone is sluggish at best under normal conditions. We now report that this reaction can be effected in moderate yield under high pressure. Thus, 2,6-dichloro-4-pyridyl-(N-prop-2-ynyl)carboxamidine (4b) was reacted with three α-substituted-β-ketoesters (2b-d) at 10–16 kbar to afford herbicidal 2-(2,6-dichloro-4-pyridyl)-3-(prop-2-ynyl)-4(3H)-pyrimidinones 5b and 5c in 15 - 43% yield. This result

  N-单取代的idine与β-酮酸酯的反应得到嘧啶酮的反应在正常条件下最好是缓慢的。现在我们报告该反应可以在高压下以中等收率进行。因此，在10-16 kbar下，将2,6-二氯-4-吡啶基-（N-丙-2-炔基）羧am（4b）与三种α-取代-β-酮酸酯（2b-d）反应，得到除草剂2 -（2，6-二氯-4-吡啶基）-3-（丙-2-炔基）-4（3 H）-嘧啶酮5b和5c，产率为15-43％。该结果扩大了通过施加高压促进的反应范围。
• Process for pyrimidinone compounds
  申请人：Rohm and Haas Company

  公开号：US06054582A1

  公开（公告）日：2000-04-25

  This invention relates to a process for the preparation of pyrimidinone compounds of the formula ##STR1## wherein Ar is an optionally substituted aryl or heteroaromatic moiety, R.sup.3 is an optionally substituted alkyl, alkenyl or alkynyl, R.sup.5 is a hydrogen atom, halo, cyano or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy or alkylthio, and R.sup.6 is a hydrogen atom, cyano, or an optionally substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl or heteroaryl. The process comprises reaction of an amidine and a malonic acid derivative to give a hydroxypyrimidinone followed by conversion of the resulting hydroxypyrimidinone to a sulfonyloxypyrimidinone followed by reaction of the resulting sulfonyloxypyrimidinone with an organometallic reagent to give the desired pyrimidinone. The hydroxypyrimidinones, wherein R.sup.6 is hydroxy and sulfonyloxypyrimidinones wherein R.sup.6 is a substituted sulfonyloxy moiety, are themselves new and useful intermediates in the preparation of the desired pyrimidinones.

  本发明涉及一种制备嘧啶酮化合物的方法，其化学式为##STR1##其中Ar是可选取代的芳基或杂环芳基部分，R.sup.3是可选取代的烷基，烯基或炔基，R.sup.5是氢原子，卤素，氰基或可选取代的烷基，烯基，炔基，烷氧基或烷硫基，而R.sup.6是氢原子，氰基或可选取代的烷基，环烷基，烯基，炔基，芳基，芳基烷基或杂环芳基。该方法包括将一种酰胺和一种马来酸衍生物反应以得到一种羟基嘧啶酮，随后将所得的羟基嘧啶酮转化为磺酰氧基嘧啶酮，然后将所得的磺酰氧基嘧啶酮与有机金属试剂反应以得到所需的嘧啶酮。其中R.sup.6为羟基的羟基嘧啶酮和R.sup.6为取代磺酰氧基的磺酰氧基嘧啶酮本身是制备所需的嘧啶酮的新型有用中间体。
• 6-Trifluoromethanesulfonyloxy-4(3H)-pyrimidinones as versatile intermediates for the synthesis of 6-functionalized 4(3H)-pyrimidinones
  作者：Edward C Taylor、Ping Zhou、Colin M Tice

  DOI：10.1016/s0040-4039(97)00947-7

  日期：1997.6

  The reaction of 6-trifluoromethanesulfonyloxy-4(3H)-pyrimidinones with Me2Cu(CN)Li-2, and with vinyl tributyltin, trimethylsilylacetylene, and zinc cyanide with palladium catalysis, are described for the synthesis of a variety of fully functionalized 6-substituted-4(3H)-pyrimidinones of interest as herbicides.
• US5889184A
  申请人：——

  公开号：US5889184A

  公开（公告）日：1999-03-30