6-amino-1,3-dimethyl-5-[(phenylimino)methyl]uracil | 132124-82-4

• 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: 6-amino-1,3-dimethyl-5-[(phenylimino)methyl]uracil
• 英文别名: 6-Amino-1,3-dimethyl-5-(phenyliminomethyl)pyrimidine-2,4-dione
• CAS: 132124-82-4
• 化学式: C₁₃H₁₄N₄O₂
• 分子量: 258.28
• InChiKey: PNPAZPWATBKGCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 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：
  79
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-amino-1,3-dimethyl-5-[(phenylimino)methyl]uracil 在 sodium tetrahydroborate 、 六氯乙烷 、 三乙胺 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 70.5h， 生成 7-(p-Tolyl)amino-6-phenyl-1,3-dimethyl-1,2,3,4,5,6-hexahydropyrimido<4,5-d>pyrimidine
  参考文献：
  名称：

  氨基磷烷介导的融合尿嘧啶的合成。一种嘧啶[4,5- d ]嘧啶衍生物的简易一锅法制备

  摘要：

  亚氨基正膦的维蒂希氮杂型反应3 [（ - ，5 Ñ -Arylimino）甲基] -6 - [（三苯基亚正膦基）氨基] -1,3-二甲基尿嘧啶，用芳香族异氰酸酯导致官能嘧啶并[4,5- d ]嘧啶4。亚氨基正膦5，从制备3通过用硼氢化钠选择性还原，通过与异氰酸酯反应进行二氢嘧啶并成环得到7-氨基-6-芳基- 1,3-二甲基-1,2,3,4,5,6-六氢嘧啶并[ 4,5- d ]嘧啶6。

  DOI：

  10.1016/s0040-4020(01)90083-3
• 作为产物：
  描述：

  5-[(dimethylamino)methylene]dihydro-6-imino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione monohydrochloride 、 苯胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以78%的产率得到6-amino-1,3-dimethyl-5-[(phenylimino)methyl]uracil
  参考文献：
  名称：

  Iodobenzene Diacetate–Promoted N–N and N–O Bond Formation for Pyrazolo- and Isoxazolopyrimidine Syntheses

  摘要：

  Pyrazolo[3,4-d]pyrimidine-4,6-dione derivatives were efficiently synthesized via the intramolecular N-N bond coupling of 5-iminomethyl-6-aminouracil derivatives using iodobenzene diacetate. The oxidative coupling was also applied to the analogous N-O bond formation producing isoxazolo[3,4-d]primidine-4,6-dione derivatives.

  DOI：

  10.3987/com-08-s(d)34

文献信息

• Reactivities of 6-Amino-1,3-dimethyl-5-thioformyluracil toward Nucleophiles and Its Application to Synthesis of Pyrido(2,3-d)pyrimidines.
  作者：Kosaku HIROTA、Keiko KUBO、Hironao SAJIKI

  DOI：10.1248/cpb.45.542

  日期：——

  The reaction of the 5-thioformyluracil 1 with phenylhydrazine and various amines readily afforded the hydrazone 3a and Schiff bases 3b-d, respectively. Further, carbanions and Wittig reagents reacted with 1 to give pyrido[2, 3-d]pyrimidines 4 and 9. The corresponding 5-formyluracil 2 possessed much lower reactivities toward these nucleophiles than did 1.

  5-硫代甲酰尿嘧啶1与苯肼和各种胺的反应容易地分别得到腙3a和希夫碱3b-d。此外，碳负离子和维蒂希试剂与1反应得到吡啶并[2, 3-d]嘧啶4和9。相应的5-甲酰尿嘧啶2对这些亲核试剂的反应活性比1低得多。
• A New Synthesis of Pyrazolo[3,4-<i>d</i>]pyrimidine-4,6(5<i>H</i>,7<i>H</i>)-diones by Oxidative N-N Bond Formation of 6-Amino-5-(<i>N</i>-aryliminomethyl)uracils Using Iodobenzene Diacetate
  作者：Hironao Sajiki、Kazuyuki Hattori、Magoichi Sako、Kosaku Hirota

  DOI：10.1055/s-1997-1073

  日期：——

  The intramolecular cyclizations of 6-amino-5-(N-aryliminomethyl)-1,3-dimethyluracils (2) involving the N-N bond formation were effected via a hypervalent iodine oxidation using iodobenzene diacetate. This method enabled a facile synthesis of 2-aryl-5,7-dimethylpyrazolo[3,4-d]pyrirnidine-4,6(5H,7H)-diones (3) in moderate to excellent yields. The primary advantage of this N-N bond formation method is that various 2-aryl-substituted pyrazolo[3,4d]pyrimidines can be provided under mild oxidative conditions.

  6-amino-5-(N-aryliminomethyl)-1,3-dimethyluracils (2) 的分子内环化涉及 N-N 键的形成，是通过使用二乙酸碘苯的高价碘氧化作用实现的。通过这种方法，可以轻松合成 2-芳基-5,7-二甲基吡唑并[3,4-d]吡咯烷-4,6(5H,7H)-二酮 (3)，产率为中等到极佳。这种 N-N 键形成方法的主要优点是可以在温和的氧化条件下提供各种 2-芳基取代的吡唑并[3,4d]嘧啶。
• Iodobenzene Diacetate–Promoted N–N and N–O Bond Formation for Pyrazolo- and Isoxazolopyrimidine Syntheses
  作者：Hironao Sajiki、Yasunari Monguchi、Kazuyuki Hattori、Tomohiro Maegawa、Kosaku Hirota

  DOI：10.3987/com-08-s(d)34

  日期：——

  Pyrazolo[3,4-d]pyrimidine-4,6-dione derivatives were efficiently synthesized via the intramolecular N-N bond coupling of 5-iminomethyl-6-aminouracil derivatives using iodobenzene diacetate. The oxidative coupling was also applied to the analogous N-O bond formation producing isoxazolo[3,4-d]primidine-4,6-dione derivatives.
• Iminophosphorane-mediated synthesis of fused uracils. A faclle one-pot preparation of pyrimido[4,5-d]pyrimidine derivatives
  作者：Pedro Molina、Maria Jesús Vilaplana、Juana Pérez

  DOI：10.1016/s0040-4020(01)90083-3

  日期：1990.1

  uracils, with aromatic isocyanates leads to the functionalized pyrimido[4,5-d]pyrimidines 4. Iminophosphoranes 5, prepared from 3 by selective reduction with sodium borohydride, undergo dihydropyrimido annelation by reaction with isocyanates to give 7-amino-6-aryl-1,3-dimethyl-1,2,3,4,5,6-hexahydropyrimido[4,5-d]pyrimidines 6.

  亚氨基正膦的维蒂希氮杂型反应3 [（ - ，5 Ñ -Arylimino）甲基] -6 - [（三苯基亚正膦基）氨基] -1,3-二甲基尿嘧啶，用芳香族异氰酸酯导致官能嘧啶并[4,5- d ]嘧啶4。亚氨基正膦5，从制备3通过用硼氢化钠选择性还原，通过与异氰酸酯反应进行二氢嘧啶并成环得到7-氨基-6-芳基- 1,3-二甲基-1,2,3,4,5,6-六氢嘧啶并[ 4,5- d ]嘧啶6。