1-[4-氨基-2-(4-氯苯基)-6-甲基嘧啶-5-基]乙酮 | 130102-91-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[4-氨基-2-(4-氯苯基)-6-甲基嘧啶-5-基]乙酮
• 英文名称: 5-acetyl-4-amino-2-(4-chlorophenyl)-6-methylpyrimidine
• 英文别名: 1-[4-Amino-2-(4-chlorophenyl)-6-methylpyrimidin-5-yl]ethanone
• CAS: 130102-91-9
• 化学式: C₁₃H₁₂ClN₃O
• 分子量: 261.711
• InChiKey: MEYDQTXPLFHAEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[4-氨基-2-(4-氯苯基)-6-甲基嘧啶-5-基]乙酮 在 sodium methylate 作用下， 以 甲苯 、 正丁醇 为溶剂， 反应 10.67h， 生成 2-(4-chlorophenyl)-4,5-dimethyl-6-phenylpyrido[2,3-d]pyrimidin-7(8H)-one
  参考文献：
  名称：

  从 5-合成新的吡啶并[2,3-d]嘧啶-5-one、吡啶并[2,3-d]嘧啶-7-one和嘧啶并[4,5-d][1,3]恶嗪衍生物乙酰-4-氨基嘧啶

  摘要：

  开发了合成新的吡啶并[2,3- d ]嘧啶和嘧啶并[4,5- d ][1,3]恶嗪衍生物的方法。当与 MeONa 在 BuOH 中回流加热时，​​用羧酸酐或酰氯酰化的 5-乙酰基-4-氨基嘧啶转化为吡啶并[2,3 - d ]嘧啶-5-酮衍生物，即乙酰甲基和酰胺羰基部分参与环化。在活化的CH的存在2基团（例如。，物理信道2）在酰胺部分中，环化包括该组和乙酰羰基引起吡啶并[2,3- d]嘧啶-7-one衍生物。5-乙酰基-4-氨基嘧啶与羧酸氯化物在二甲苯中回流反应，然后加入碱，得到嘧啶并[4,5- d ][1,3]恶嗪。

  DOI：

  10.1007/s10593-021-02982-8
• 作为产物：
  描述：

  乙酰丙酮 、 4-chloro-N-cyano-benzamidine 在 nickel diacetate 作用下， 反应 5.0h， 以51%的产率得到1-[4-氨基-2-(4-氯苯基)-6-甲基嘧啶-5-基]乙酮
  参考文献：
  名称：

  摘要：

  A method for the synthesis of methyl and ethyl 2-R-1-4-R-2-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-7-carboxylates was proposed. The method is based on condensation of 2-R-1-6-R-2-5-acetyl-4-aminopyrimidines with ethyl oxalate in the presence of MeONa or EtONa. Products of the Friedlander self-condensation of the starting pyrimidines were also obtained.

  DOI：

  10.1023/a:1021304619076

文献信息

• Synthesis of new pyrido[2,3-d]pyrimidine derivatives by three-component condensation of 5-acetyl-4-aminopyrimidines, cyclohexane-1,3-diones, and orthocarboxylic acid esters
  作者：A. V. Komkov、M. A. Prezent、A. V. Ignatenko、I. P. Yakovlev、V. A. Dorokhov

  DOI：10.1007/s11172-006-0552-0

  日期：2006.11

  derivatives with dimedone (or cyclohexane-1,3-dione) and triethyl orthoacetate (or triethyl orthopropionate) gave derivatives of 7-(1,3-dioxocyclohex-2-ylidene)-7,8-dihydropyrido[2,3-d]pyrimidine. These heterocyclic compounds containing the enamino ketone fragment can form boron chelates under the action of butoxy(diphenyl)borane.

  5-乙酰-4-氨基嘧啶衍生物与二甲酮（或环己烷-1,3-二酮）和原乙酸三乙酯（或原丙酸三乙酯）的三组分缩合得到7-（1,3-二氧环己-2-亚基）衍生物-7,8-二氢吡啶并[2,3-d]嘧啶。这些含有烯氨基酮片段的杂环化合物在丁氧基（二苯基）硼烷的作用下可以形成硼螯合物。
• Synthesis of pyrido[2,3-d]pyrimidin-7(8H)-one derivatives from 5-acetyl-4-aminopyrimidines and β-dicarbonyl compounds
  作者：A. V. Komkov、I. P. Yakovlev、V. A. Dorokhov

  DOI：10.1007/s11172-005-0320-6

  日期：2005.3

  Heating of 5-acetyl-4-aminopyrimidine derivatives with ethyl acetoacetate, ethyl benzoylacetate, and diethyl acetone-1, 3-dicarboxylate in the absence of a base gave the corresponding 6-acylpyrido[2, 3-d]pyrimidin-7(8H)-ones. Under analogous conditions, the reaction with ethyl malonate afforded ethyl 7-oxo-7, 8-dihydropyrido[2, 3-d]pyrimidine-6-carboxylates. The pyridone (rather than hydroxypyridine)

  5-乙酰基-4-氨基嘧啶衍生物与乙酰乙酸乙酯、苯甲酰乙酸乙酯和二乙基丙酮-1, 3-二羧酸在无碱存在下加热得到相应的6-酰基吡啶并[2, 3-d]嘧啶-7(8H) ）-那些。在类似条件下，与丙二酸乙酯反应得到7-氧代-7, 8-二氢吡啶并[2, 3-d]嘧啶-6-羧酸乙酯。获得的吡啶并嘧啶的吡啶酮（而不是羟基吡啶）结构通过红外光谱证实。
• 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。
• Synthesis of new pyrido[2,3-d]pyrimidin-5-one, pyrido[2,3-d]pyrimidin-7-one, and pyrimidino[4,5-d][1,3]oxazine derivatives from 5-acetyl-4-aminopyrimidines
  作者：Alexander V. Komkov、Mikhail A. Kozlov、Andrey S. Dmitrenok、Nataliya G. Kolotyrkina、Mikhail E. Minyaev、Igor V. Zavarzin

  DOI：10.1007/s10593-021-02982-8

  日期：2021.8

  Methods were developed for the synthesis of new pyrido[2,3-d]pyrimidine and pyrimidino[4,5-d][1,3]oxazine derivatives. When heated under reflux with MeONa in BuOH, 5-acetyl-4-aminopyrimidines, acylated with carboxylic anhydrides or acid chlorides, are transformed into pyrido[2,3-d]pyrimidin-5-one derivatives, i.e., the acetyl methyl group and the amide carbonyl moiety are involved in the cyclization

  开发了合成新的吡啶并[2,3- d ]嘧啶和嘧啶并[4,5- d ][1,3]恶嗪衍生物的方法。当与 MeONa 在 BuOH 中回流加热时，​​用羧酸酐或酰氯酰化的 5-乙酰基-4-氨基嘧啶转化为吡啶并[2,3 - d ]嘧啶-5-酮衍生物，即乙酰甲基和酰胺羰基部分参与环化。在活化的CH的存在2基团（例如。，物理信道2）在酰胺部分中，环化包括该组和乙酰羰基引起吡啶并[2,3- d]嘧啶-7-one衍生物。5-乙酰基-4-氨基嘧啶与羧酸氯化物在二甲苯中回流反应，然后加入碱，得到嘧啶并[4,5- d ][1,3]恶嗪。
• ——
  作者：A. V. Komkov、V. A. Dorokhov

  DOI：10.1023/a:1021304619076

  日期：——

  A method for the synthesis of methyl and ethyl 2-R-1-4-R-2-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-7-carboxylates was proposed. The method is based on condensation of 2-R-1-6-R-2-5-acetyl-4-aminopyrimidines with ethyl oxalate in the presence of MeONa or EtONa. Products of the Friedlander self-condensation of the starting pyrimidines were also obtained.