2-(4-吡啶)-4-羟基-6-甲基嘧啶 | 59341-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-(4-吡啶)-4-羟基-6-甲基嘧啶
• 中文别名: 2-吡啶-4-基-4-羟基-6-甲基嘧啶
• 英文名称: 6-methyl-2-(pyridin-4'-yl)pyrimidin-4(3H)-one
• 英文别名: 6-methyl-2-pyridin-4-yl-3H-pyrimidin-4-one；6-methyl-2-(4-pyridinyl)-4-pyrimidinol；6-Methyl-2(4-pyridinyl)4-pyrimidinol；6-methyl-2-(pyridin-4-yl)pyrimidin-4(3H)-one；4-methyl-2-pyridin-4-yl-1H-pyrimidin-6-one
• CAS: 59341-68-3
• 化学式: C₁₀H₉N₃O
• mdl: MFCD00106896
• 分子量: 187.201
• InChiKey: UFMQZZRBKSOEKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-(4-吡啶)-4-羟基-6-甲基嘧啶 在 三氯氧磷 作用下， 以87%的产率得到4-氯-2-(4-吡啶)-6-甲基嘧啶
  参考文献：
  名称：

  Unfused heterobicycles as amplifiers of phleomycin. V. A range of pyridinylpyrimidines with strongly basic side chains

  摘要：

  将 3-aminocrotonamide 与吡啶-2-羧酸乙酯或相关酯类缩合后得到 6-甲基嘧啶-4(3H)-酮，每个酮的 2-位上都含有吡啶-2'-基、吡啶-3'-基、吡啶-4'-基、呋喃-2'-基 2'-基、吡啶-3'-基、吡啶-4'-基、呋喃-2'-基、呋喃-3'-基、噻吩-2'-基或吡嗪-2'-基。 或吡嗪-2'-基取代基。其中，吡啶基衍生物 (1a)、(2a) 和 (3a) (3a) 转化为它们的 4-氯类似物，然后通过亲核 置换成相应的 β-二甲氨基乙硫基、β-二甲氨基乙氨基、 β-二甲氨基乙氧基和 γ-二甲氨基丙基氨基衍生物。这些 报告了这些化合物作为夫来霉素的放大剂对大肠杆菌的活性。

  DOI：

  10.1071/ch9821203
• 作为产物：
  描述：

  4-氰基吡啶 在 sodium methylate 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 28.0h， 生成 2-(4-吡啶)-4-羟基-6-甲基嘧啶
  参考文献：
  名称：

  HIV-1结构蛋白装配抑制剂2-吡啶基嘧啶的合成与评价

  摘要：

  为了鉴定具有改善的溶解度和效力的HIV-1衣壳装配抑制剂，我们基于较早的先导化合物N-（4-（乙氧基羰基）苯基）-2-（吡啶-4-基）合成了两个嘧啶类似物系列）喹唑啉-4-胺 体外结合实验表明，我们的2-吡啶-4-基嘧啶系列的IC 50值高于28μM 。我们的2-吡啶-3-基嘧啶系列显示的IC 50值为3至60μM 。具有在4- N-苯基部分处引入的氟取代基以及在C-6处的甲基的同类物代表与衣壳蛋白的C-末端结构域结合的有效HIV衣壳装配抑制剂。

  DOI：

  10.1016/j.bmcl.2016.06.039

文献信息

• N-[2-(pyridinyl)-4-pyrimidinyl]ureas
  申请人：Sterling Drug Inc.

  公开号：US04008235A1

  公开（公告）日：1977-02-15

  Compounds useful as anti-allergic agents are N-R.sub.3 -N-R.sub.4 -N'-R-N'-(2-Q-5-R.sub.1 -6-R.sub.2 -4-pyrimidinyl)ureas (I), where Q is 4- or 3- or 2-pyridinyl or 4- or 3- or 2-pyridinyl having one or two lower-alkyl substituents or N-oxide thereof, R is hydrogen or lower-alkyl, R.sub.1 is hydrogen, lower-alkyl or cyano, R.sub.2 is hydrogen or lower-alkyl, R.sub.3 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R.sub.4 is hydrogen, lower-alkyl, lower-hydroxyalkyl, lower-alkenyl or lower-cycloalkyl. Said ureas are prepared by reacting 2-Q-4-RNH-5-R.sub.1 -6-R.sub.2 -pyrimidine (II) with a carbamylating agent selected from an R.sub.4 '-isocyanate of the formula R.sub.4 'N=C=O to produce N-R.sub.4 '-N'-R-N'-(2-Q-5-R.sub.1 -6-R.sub.2 -4-pyrimidinyl)urea (IA), an N-R.sub.3 '-N-R.sub.4 '-carbamyl halide of the formula R.sub.3 'R.sub.4 'NC(=O)-halide to produce N-R.sub.3 '-N-R.sub.4 'N'-R-N'-(2-Q-5-R.sub.1 -6-R.sub.2 -4-pyrimidinyl)urea (IB) or 1,1'-carbonyldiimidazole to produce N-(2-Q-5-R.sub.1 -6-R.sub.2 -4-pyrimidinyl)-N-R-imidazole-1-carboxamide and then reacting said 1-carboxamide with R.sub.3 R.sub.4 NH to produce I.

  可用作抗过敏剂的化合物为N-R.sub.3 -N-R.sub.4 -N'-R-N'-(2-Q-5-R.sub.1 -6-R.sub.2 -4-嘧啶基)脲类化合物（I），其中Q为4-或3-或2-吡啶基或带有一个或两个较低烷基取代基或其N-氧化物，R为氢或较低烷基，R.sub.1为氢、较低烷基或氰基，R.sub.2为氢或较低烷基，R.sub.3为氢、较低烷基或较低羟基烷基，R.sub.4为氢、较低烷基、较低羟基烷基、较低烯基或较低环烷基。所述脲类化合物通过将2-Q-4-RNH-5-R.sub.1 -6-R.sub.2 -嘧啶（II）与选择自R.sub.4 'N=C=O的R.sub.4 '-异氰酸酯的羰基化试剂反应制备，以产生N-R.sub.4 '-N'-R-N'-(2-Q-5-R.sub.1 -6-R.sub.2 -4-嘧啶基)脲（IA），R.sub.3 'R.sub.4 'NC(=O)-卤化物的N-R.sub.3 '-N-R.sub.4 '-脲基卤化物以产生N-R.sub.3 '-N-R.sub.4 'N'-R-N'-(2-Q-5-R.sub.1 -6-R.sub.2 -4-嘧啶基)脲（IB）或1,1'-羰基二咪唑以产生N-(2-Q-5-R.sub.1 -6-R.sub.2 -4-嘧啶基)-N-R-咪唑-1-甲酰胺，然后将所述1-甲酰胺与R.sub.3 R.sub.4 NH反应以产生I。
• 5,8-Dihydro-5-oxo-2-(4-or
  申请人：Sterling Drug Inc.

  公开号：US03992380A1

  公开（公告）日：1976-11-16

  Antibacterial 5,8-dihydro-8-(lower-alkyl)-5-oxo-2-Q-4-R.sub.2 -6-Z-pyrido[2,3-d]pyrimidine (I) where Z is carboxy or lower-carbalkoxy, R.sub.2 is hydrogen or lower-alkyl and Q is 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents is prepared by heating di-(lower-alkyl) N-(2-Q-6-R.sub.2 -4-pyrimidinyl)aminomethylenemalonate (III) to produce 5,8-dihydro-5-oxo-2-Q-4-R.sub.2 -6-Z-pyrido[2,3-d]pyrimidine (II) which is tautomeric with 5-hydroxy-2-Q-4-R.sub.2 -6-Z-pyrido[2,3-d]pyrimidine (IIA) where Q and R.sub.2 are the same as in I above and Z is lower-carbalkoxy, reacting II(or IIA) with a lower-alkylating agent to produce I where Z is lower-carbalkoxy and hydrolyzing this ester (I) to produce I where Z is carboxy. Alternatively, the acid (II or IIA where Z is COOH) can be alkylated after first hydrolyzing the ester (II or IIA where Z is lower-carbalkoxy). The preparations of the intermediate III and intermediates used in its preparation are given.

  抗菌性5,8-二氢-8-(较低烷基)-5-氧代-2-Q-4-R.sub.2-6-Z-吡啶并[2,3-d]嘧啶(I)，其中Z为羧基或较低羧烷氧基，R.sub.2为氢或较低烷基，Q为4(或3)-吡啶基或带有一个或两个较低烷基取代基的4(或3)-吡啶基，通过加热二-(较低烷基)N-(2-Q-6-R.sub.2-4-嘧啶基)氨甲亚甲基丙二酸酯(III)制备，以产生5,8-二氢-5-氧代-2-Q-4-R.sub.2-6-Z-吡啶并[2,3-d]嘧啶(II)，其与5-羟基-2-Q-4-R.sub.2-6-Z-吡啶并[2,3-d]嘧啶(IIA)互变异构，其中Q和R.sub.2与上述I中相同，Z为较低羧烷氧基，将II(或IIA)与较低烷基化试剂反应以产生I，其中Z为较低羧烷氧基，并水解此酯(I)以产生Z为羧基的I。或者，酸(II或IIA，其中Z为COOH)在首先水解酯(II或IIA，其中Z为较低羧烷氧基)后可以被烷基化。给出了中间体III及其制备中使用的中间体的制备方法。
• Unfused heterobicycles as amplifiers of phleomycin. V. A range of pyridinylpyrimidines with strongly basic side chains
  作者：DJ Brown、WB Cowden

  DOI：10.1071/ch9821203

  日期：——

  The condensation of 3-aminocrotonamide with ethyl pyridine-2-carboxylate or a related ester gave 6-methylpyrimidin-4(3H)-ones, each bearing at its 2-position a pyridin-2'-yl, pyridin-3'-yl, pyridin- 4'-yl, furan-2'-yl, furan-3'-yl, thien-2'-yl or pyrazin-2'-yl substituent. Of these, the pyridinyl derivatives (1a), (2a) and (3a) were converted into their 4-chloro analogues and thence by nucleophilic displacement into the corresponding β-dimethylaminoethylthio, β-dimethylaminoethylamino, β-dimethylaminoethoxy and γ-dimethylaminopropylamino derivatives. The activities of these compounds as amplifiers of phleomycin against Escherichia coli are reported.

  将 3-aminocrotonamide 与吡啶-2-羧酸乙酯或相关酯类缩合后得到 6-甲基嘧啶-4(3H)-酮，每个酮的 2-位上都含有吡啶-2'-基、吡啶-3'-基、吡啶-4'-基、呋喃-2'-基 2'-基、吡啶-3'-基、吡啶-4'-基、呋喃-2'-基、呋喃-3'-基、噻吩-2'-基或吡嗪-2'-基。 或吡嗪-2'-基取代基。其中，吡啶基衍生物 (1a)、(2a) 和 (3a) (3a) 转化为它们的 4-氯类似物，然后通过亲核 置换成相应的 β-二甲氨基乙硫基、β-二甲氨基乙氨基、 β-二甲氨基乙氧基和 γ-二甲氨基丙基氨基衍生物。这些 报告了这些化合物作为夫来霉素的放大剂对大肠杆菌的活性。
• A convenient synthesis of pyrimidinone and pyrimidine containing bisheteroarenes and analogs
  作者：Hardesh K. Maurya、Atul Gupta

  DOI：10.1039/c4ra01689k

  日期：——

  The synthesis of pyrimidinone containing bisheteroarenes (3) and related analogs (9 and 10) by the reaction of active methylenes or substituted methyl acrylate with nitrogen containing precursors viz. amidines, or thiourea in water as well as other organic solvents was studied. Synthesized compounds have further been explored for the synthesis of diversified pyrimidines 4, 6–8, 11, 12 and 14 through

  通过活性亚甲基或取代的丙烯酸甲酯与含氮前体的反应合成含双嘧啶酮的嘧啶酮（3）和相关类似物（9和10）。water以及其他有机溶剂中的或硫脲进行了研究。合成的化合物已进一步探讨了多元化嘧啶的合成4，6-8，11，12和14通过一个顺序方法。
• Novel orally active inhibitors of passive cutaneous anaphylaxis in rats: N-[2-(4-Pyridinyl)-4-pyrimidinyl] ureas and dialkyl [[[2-(4-pyridinyl)-4-pyrimidinyl]amino]methylene]malonates
  作者：George Y. Lesher、Baldev Singh、Zigurd Mielens

  DOI：10.1021/jm00349a014

  日期：1982.7

  4-Chloro-2-(4-pyridinyl)pyrimidines were treated with alkylamines to afford the corresponding N-substituted amino derivatives. 4-Amino-2-(4-pyridinyl)pyrimidines and their N-substituted analogues were converted to amides, carbamates, aminomethylenemalonates, and ureas. Many of these compounds were found to have potential antiallergic activity as indicated by the rat passive cutaneous anaphylaxis screen. The most compounds were found in the last two series.