N-(5-acetyl-6-methyl-2-phenylpyrimidin-4-yl)benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(5-acetyl-6-methyl-2-phenylpyrimidin-4-yl)benzamide
• 英文别名: CBL-17
• 化学式: C₂₀H₁₇N₃O₂
• 分子量: 331.374
• InChiKey: NWOXBWXLABRUES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(5-acetyl-6-methyl-2-phenylpyrimidin-4-yl)benzamide 在 sodium methylate 作用下， 以 正丁醇 为溶剂， 反应 0.17h， 以64%的产率得到4-Methyl-2,7-diphenyl-8H-pyrido[2,3-d]pyrimidin-5-one
  参考文献：
  名称：

  Efficient methods for the synthesis of pyrido[2,3-d]pyrimidin-5-ones from 4-amino-5-acetylpyrimidines

  摘要：

  New methods for annelation of a pyridine ring to a pyrimidine ring were suggested. Substituted 8H-pyrido[2,3-d]pyrimidin-5-ones (8a-f) were synthesized by the interaction of 2,6-disubstituted 4-amino-5-acetylpyrimidines (1-4) with formamide or acetamide acetals followed by cyclization under the action of sodium methoxide in methanol. 2,4-Disubstituted 7-phenyl-8H-pyrido[2,3-d]pyrimidin-5-ones (11a-c) were prepared by the reaction of 2,6-disubstituted 5-acetyl-4-benzoylaminopyrimidines (10a-c) with MeONa in boiling BuOH.

  DOI：

  10.1007/bf00703702
• 作为产物：
  描述：

  1-(4-氨基-6-甲基-2-苯基嘧啶-5-基)乙酮 、 苯甲酸酐 以 甲苯 为溶剂， 反应 16.0h， 以65%的产率得到N-(5-acetyl-6-methyl-2-phenylpyrimidin-4-yl)benzamide
  参考文献：
  名称：

  Efficient methods for the synthesis of pyrido[2,3-d]pyrimidin-5-ones from 4-amino-5-acetylpyrimidines

  摘要：

  New methods for annelation of a pyridine ring to a pyrimidine ring were suggested. Substituted 8H-pyrido[2,3-d]pyrimidin-5-ones (8a-f) were synthesized by the interaction of 2,6-disubstituted 4-amino-5-acetylpyrimidines (1-4) with formamide or acetamide acetals followed by cyclization under the action of sodium methoxide in methanol. 2,4-Disubstituted 7-phenyl-8H-pyrido[2,3-d]pyrimidin-5-ones (11a-c) were prepared by the reaction of 2,6-disubstituted 5-acetyl-4-benzoylaminopyrimidines (10a-c) with MeONa in boiling BuOH.

  DOI：

  10.1007/bf00703702

文献信息

• Synthesis of new 5-hydroxyquinazoline derivatives from functionalized 5-acetyl-6-methylpyrimidines
  作者：Alexander V. Komkov、Mikhail A. Kozlov、Yurii A. Linitskii、Leonid S. Vasil’ev、Andrey S. Dmitrenok、Igor V. Zavarzin

  DOI：10.1007/s10593-021-02981-9

  日期：2021.8

  A new method for the synthesis of quinazolines based on the annulation of the benzene ring to 5-acetyl-6 methylpyrimidin-2-one(thione) derivatives has been proposed. Condensation of the latter at the methyl group with dimethylformamide dimethyl acetal in boiling PhH leads to the formation of 5-acetyl-6-[2-(dimethylamino)vinyl]pyrimidin-2-ones(thiones), which, when boiled with MeONa in MeOH, cyclize

  提出了一种基于苯环环化为 5-乙酰基-6 甲基嘧啶-2-酮（硫酮）衍生物合成喹唑啉的新方法。后者在沸腾的 PhH 中与二甲基甲酰胺二甲基缩醛在甲基上的缩合导致形成 5-乙酰基-6-[2-（二甲氨基）乙烯基]嘧啶-2-酮（硫酮），当与 MeONa 一起煮沸时， MeOH，环化为 5-羟基喹唑啉-2-酮（硫酮）。类似地，5-乙酰基-6-甲基-4-(三氟甲基)嘧啶转化为5-羟基-4-(三氟甲基)喹唑啉。喹唑啉不是由 5-乙酰基-6-甲基嘧啶与二甲基甲酰胺二甲基缩醛在乙酰基上缩合而成，但 5-乙酰基-6-甲基嘧啶可用于获得吡啶并[2,3- d ]嘧啶衍生物。
• Synthesis of novel pyrimido[4,5-d]pyrimidine derivatives from 5-acetyl-4-aminopyrimidines
  作者：Alexander V. Komkov、Mikhail А. Kozlov、Mikhail А. Prezent、Andrey S. Dmitrenok、Natalya G. Kolotyrkina、Mikhail E. Minyaev、Igor V. Zavarzin

  DOI：10.1007/s10593-022-03078-7

  日期：2022.5

  Two routes were proposed for the synthesis of pyrimido[4,5-d]pyrimidine derivatives from 5-acetyl-4-aminopyrimidines. Acylation of 5-acetyl-4-aminopyrimidines followed by cyclization by the action of NH4OAc made it possible to access pyrimido[4,5-d]pyrimidines with alkyl, aryl, and hetaryl substituents in positions 2 and 7. Reductive amination of the acetyl group in 5-acetyl-4-aminopyrimidines and

  提出了两种从 5-乙酰基-4-氨基嘧啶合成嘧啶并[4,5- d ]嘧啶衍生物的路线。5-乙酰基-4-氨基嘧啶的酰化，然后通过 NH4OAc 的作用进行环化，使得在 2 位和 7 位上具有烷基、芳基和杂芳基取代基的嘧啶并[4,5- d ] 嘧啶成为可能。乙酰基的还原胺化在 5-乙酰基-4-氨基嘧啶中的基团和随后与 DMF-DMA 或 HC(OEt) 3的环化导致形成 6-烷基-3,4-二氢嘧啶并[4,5- d ]嘧啶。
• Komkow A. W., Ugrak B. I., Bogdanow W. S., Dorokhow W A., Isw. AN. Ser. khim, (1994) N 8, S 1469-1474
  作者：Komkow A. W., Ugrak B. I., Bogdanow W. S., Dorokhow W A.

  DOI：——

  日期：——
• Efficient methods for the synthesis of pyrido[2,3-d]pyrimidin-5-ones from 4-amino-5-acetylpyrimidines
  作者：A. V. Komkov、B. I. Ugrak、V. S. Bogdanov、V. A. Dorokhov

  DOI：10.1007/bf00703702

  日期：1994.8

  New methods for annelation of a pyridine ring to a pyrimidine ring were suggested. Substituted 8H-pyrido[2,3-d]pyrimidin-5-ones (8a-f) were synthesized by the interaction of 2,6-disubstituted 4-amino-5-acetylpyrimidines (1-4) with formamide or acetamide acetals followed by cyclization under the action of sodium methoxide in methanol. 2,4-Disubstituted 7-phenyl-8H-pyrido[2,3-d]pyrimidin-5-ones (11a-c) were prepared by the reaction of 2,6-disubstituted 5-acetyl-4-benzoylaminopyrimidines (10a-c) with MeONa in boiling BuOH.