4-(N,N-Benzylmethylamino)-6-(N-isopropylamino)-2-methylthio-5-nitropyrimidine | 618863-11-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(N,N-Benzylmethylamino)-6-(N-isopropylamino)-2-methylthio-5-nitropyrimidine
• 英文别名: 4-N-benzyl-4-N-methyl-2-methylsulfanyl-5-nitro-6-N-propan-2-ylpyrimidine-4,6-diamine
• CAS: 618863-11-9
• 化学式: C₁₆H₂₁N₅O₂S
• 分子量: 347.441
• InChiKey: FGEYKJXAVDBEQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(N,N-Benzylmethylamino)-6-(N-isopropylamino)-2-methylthio-5-nitropyrimidine 在 chromium dichloride 、 甲烷磺酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 4-[6-(Benzyl-methyl-amino)-9-isopropyl-8-methyl-9H-purin-2-yl]-piperazine-1-carboxylic acid ethyl ester
  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：

  异丙胺 、 N-甲基苄胺 、 2-甲硫基-4,6-二氯-5-硝基嘧啶 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 以98%的产率得到4-(N,N-Benzylmethylamino)-6-(N-isopropylamino)-2-methylthio-5-nitropyrimidine
  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.