4-amino-6-chloro-1-methylpyrimidin-2-one | 90801-04-0

• 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: 4-amino-6-chloro-1-methylpyrimidin-2-one
• 英文别名: 4-Chlor-6-amino-2-oxo-3-methyl-dihydro-pyrimidin；4-amino-6-chloro-1-methyl-1H-pyrimidin-2-one；4-Amino-6-chloro-1-methylpyrimidin-2-one
• CAS: 90801-04-0
• 化学式: C₅H₆ClN₃O
• 分子量: 159.575
• InChiKey: IZJYJHCUCHTAKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-amino-6-chloro-1-methylpyrimidin-2-one 在 盐酸 、 四(三苯基膦)钯 、 sodium carbonate 、 sodium nitrite 作用下， 以 丙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.5h， 生成 4-amino-5-((3',4'-dimethoxy-[1,1'-biphenyl]-4-yl)diazenyl)-1-methyl-6-(pepridin-1-yl)pyrimidin-2-one
  参考文献：
  名称：

  Synthesis of Potential Pyrimidine Derivatives via Suzuki Cross-Coupling Reaction as HIV and Kinesin Eg5 Inhibitors

  摘要：

  A series of 4-amino-5-((4-chlorophenyl)diazenyl)-6-(alkylamino)-1-methylpyrimidin-2-one deri- vatives 7-16 were prepared by nucleophilic displacement of 6-chloro-pyrimidine 6 by various amines. 4-Amino-5-((aryl-4-yl)diazenyl)-6-aryl-1-methylpyrimidin-2-one analogs 19-27, as well as 4-amino-5-((aryl-[1,1 '-biphenyl]-4-yl)diazenyl)-6-aryl-1-methylpyrimidin-2-one 29-31 and 4-amino-6-aryl-1-methylpyrimidin-2-one 34-34, were synthesized via Suzuki cross-coupling reaction, using Pd(PPh3)(4) as a catalyst and arylboronic acids as reagents. All compounds were evaluated for their antiviral activity against the replication of HIV-1 and HIV-2 in MT-4. Compounds 6, 16, 27, and 29 showed a 50% effective concentration of >2.15, >3.03, >2.29, and >1.63 mu M, respectively, but no selectivity was observed (selectivity index < 1). Two of the newly synthesized pyrimidines 12 and 29 exhibited moderate kinesin Eg5 inhibition.

  DOI：

  10.1080/15257770.2014.880475
• 作为产物：
  描述：

  6-氨基-3-甲基尿嘧啶 在 三氯氧磷 作用下， 以80%的产率得到4-amino-6-chloro-1-methylpyrimidin-2-one
  参考文献：
  名称：

  Pyrimidine to guanine PDE inhibitors: determination of chemical course via structure elucidation

  摘要：

  Structure elucidation of several new pyrimidines containing a varying extent of hydrogen bonding allowed for determination of the course of chemical reactions towards the preparation of novel substituted pyrimidines. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00340-x

文献信息

• Synthesis of Potential Pyrimidine Derivatives via Suzuki Cross-Coupling Reaction as HIV and Kinesin Eg5 Inhibitors
  作者：Najim A. Al-Masoudi、Ali G. Kassim、Nabeel A. Abdul-Reda

  DOI：10.1080/15257770.2014.880475

  日期：2014.3.4

  A series of 4-amino-5-((4-chlorophenyl)diazenyl)-6-(alkylamino)-1-methylpyrimidin-2-one deri- vatives 7-16 were prepared by nucleophilic displacement of 6-chloro-pyrimidine 6 by various amines. 4-Amino-5-((aryl-4-yl)diazenyl)-6-aryl-1-methylpyrimidin-2-one analogs 19-27, as well as 4-amino-5-((aryl-[1,1 '-biphenyl]-4-yl)diazenyl)-6-aryl-1-methylpyrimidin-2-one 29-31 and 4-amino-6-aryl-1-methylpyrimidin-2-one 34-34, were synthesized via Suzuki cross-coupling reaction, using Pd(PPh3)(4) as a catalyst and arylboronic acids as reagents. All compounds were evaluated for their antiviral activity against the replication of HIV-1 and HIV-2 in MT-4. Compounds 6, 16, 27, and 29 showed a 50% effective concentration of >2.15, >3.03, >2.29, and >1.63 mu M, respectively, but no selectivity was observed (selectivity index < 1). Two of the newly synthesized pyrimidines 12 and 29 exhibited moderate kinesin Eg5 inhibition.
• Pyrimidine to guanine PDE inhibitors: determination of chemical course via structure elucidation
  作者：Dinesh Gala、Donald J DiBenedetto、Max Kugleman、Mohindar S Puar

  DOI：10.1016/s0040-4039(03)00340-x

  日期：2003.3

  Structure elucidation of several new pyrimidines containing a varying extent of hydrogen bonding allowed for determination of the course of chemical reactions towards the preparation of novel substituted pyrimidines. (C) 2003 Elsevier Science Ltd. All rights reserved.