4-(N,N-Benzylmethylamino)-6-(N-isopropylamino)-5-nitro-2-piperidinylpyrimidine | 618863-12-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4-(N,N-Benzylmethylamino)-6-(N-isopropylamino)-5-nitro-2-piperidinylpyrimidine
• 英文别名: 4-N-benzyl-4-N-methyl-5-nitro-2-piperidin-1-yl-6-N-propan-2-ylpyrimidine-4,6-diamine
• CAS: 618863-12-0
• 化学式: C₂₀H₂₈N₆O₂
• 分子量: 384.481
• InChiKey: QHPUWWFIACSTBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  原乙酸三甲酯 、 4-(N,N-Benzylmethylamino)-6-(N-isopropylamino)-5-nitro-2-piperidinylpyrimidine 在 chromium dichloride 、 甲烷磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 以85%的产率得到9-Isopropyl-8-methyl-6-N,N-methylbenzylamino-2-piperidinylpurine
  参考文献：
  名称：

  Utility of 4,6-dichloro-2-(methylthio)-5-nitropyrimidine. Part 2: Solution phase synthesis of tetrasubstituted purines

  摘要：

  A simple synthesis of tetrasubstituted purines is disclosed based on the solution phase elaboration of 4,6-dichloro-2-methylthio-5-nitropyrimidine. One-pot sequential C4 and C6 chloride substitution by secondary and primary amines yields 4.6-diamino-2-methylthio-5-nitropyrimidines. mCPBA-mediated oxidation of the methylthio moiety to the corresponding sulfone allows facile substitution at the 2-position. CrCl2 assisted reduction of the nitro group, followed by acid catalyzed orthoester cyclization, then provides novel tetrasubstituted purines not accessible by other methods. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.112
• 作为产物：
  描述：

  N-甲基苄胺 在 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.33h， 生成 4-(N,N-Benzylmethylamino)-6-(N-isopropylamino)-5-nitro-2-piperidinylpyrimidine
  参考文献：
  名称：

  Utility of 4,6-dichloro-2-(methylthio)-5-nitropyrimidine. Part 2: Solution phase synthesis of tetrasubstituted purines

  摘要：

  A simple synthesis of tetrasubstituted purines is disclosed based on the solution phase elaboration of 4,6-dichloro-2-methylthio-5-nitropyrimidine. One-pot sequential C4 and C6 chloride substitution by secondary and primary amines yields 4.6-diamino-2-methylthio-5-nitropyrimidines. mCPBA-mediated oxidation of the methylthio moiety to the corresponding sulfone allows facile substitution at the 2-position. CrCl2 assisted reduction of the nitro group, followed by acid catalyzed orthoester cyclization, then provides novel tetrasubstituted purines not accessible by other methods. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.112

文献信息

• Utility of 4,6-dichloro-2-(methylthio)-5-nitropyrimidine. Part 2: Solution phase synthesis of tetrasubstituted purines
  作者：Lars G.J. Hammarström、Michael E. Meyer、David B. Smith、Francisco X. Talamás

  DOI：10.1016/j.tetlet.2003.09.112

  日期：2003.11

  A simple synthesis of tetrasubstituted purines is disclosed based on the solution phase elaboration of 4,6-dichloro-2-methylthio-5-nitropyrimidine. One-pot sequential C4 and C6 chloride substitution by secondary and primary amines yields 4.6-diamino-2-methylthio-5-nitropyrimidines. mCPBA-mediated oxidation of the methylthio moiety to the corresponding sulfone allows facile substitution at the 2-position. CrCl2 assisted reduction of the nitro group, followed by acid catalyzed orthoester cyclization, then provides novel tetrasubstituted purines not accessible by other methods. (C) 2003 Elsevier Ltd. All rights reserved.