2-amino-6-<(4-methylphenyl)sulfanyl>purine

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-amino-6-<(4-methylphenyl)sulfanyl>purine
• 英文别名: 2-amino-6-[(4-methylphenyl)thio]purine；6-[(4-methylphenyl)sulfanyl]-9H-purin-2-amine；6-(4-methylphenyl)sulfanyl-7H-purin-2-amine
• 化学式: C₁₂H₁₁N₅S
• mdl: MFCD19982800
• 分子量: 257.319
• InChiKey: YWDDOKOPAXEOOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-溴丙烷-1,1,1-三羧酸三乙酯 、 2-amino-6-<(4-methylphenyl)sulfanyl>purine 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以82%的产率得到2-[2-(2-amino-6-p-tolylthiopurine-9-yl)ethyl]-2-ethoxycarbonylmalonic acid diethyl ester
  参考文献：
  名称：

  AN IMPROVED PROCESS FOR THE PREPARATION OF PURINES

  摘要：

  本发明涉及一种制备嘌呤的方法。更具体地，它涉及制备公式（1）中的嘌呤，其中X是氢、硫芳基；R1和R2是氢或乙酰基。

  公开号：

  US20050215787A1
• 作为产物：
  描述：

  鸟嘌呤 、 4-甲苯硫酚 在 三氟乙酸酐 作用下， 生成 2-amino-6-<(4-methylphenyl)sulfanyl>purine
  参考文献：
  名称：

  Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9H-purine (famciclovir)

  摘要：

  Guanine 11 was converted, in a one pot reaction, into 2-amino-6-[(4-chlorophenyl)sulfanyl]purine 9a in 88% isolated yield. 4-Acetoxy-3-(acetoxymethyl)butanol 23 was prepared from 2-chloroethanol in five steps and in 46% overall yield. The mesylate ester of compound 23 reacted with 9a in the presence of potassium carbonate with a high degree of regioselectivity (89%) to give the N-9 alkylated product 26 which was isolated in 80% yield. Acidic hydrolysis of the latter compound 26 gave penciclovir 4 in virtually quantitative yield. Penciclovir 4 and famciclovir 5 were prepared from 2-amino-6-[(4-chlorophenyl)sulfanyl]puri 9a in four and five steps, respectively, by procedures involving initial alkylation with 1,2-dibromoethane. The overall yields obtained were 65 and ca. 60%, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00169-6

文献信息

• Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9H-purine (famciclovir)
  作者：Briony Brand、Colin B Reese、Quanlai Song、Cristina Visintin

  DOI：10.1016/s0040-4020(99)00169-6

  日期：1999.4

  Guanine 11 was converted, in a one pot reaction, into 2-amino-6-[(4-chlorophenyl)sulfanyl]purine 9a in 88% isolated yield. 4-Acetoxy-3-(acetoxymethyl)butanol 23 was prepared from 2-chloroethanol in five steps and in 46% overall yield. The mesylate ester of compound 23 reacted with 9a in the presence of potassium carbonate with a high degree of regioselectivity (89%) to give the N-9 alkylated product 26 which was isolated in 80% yield. Acidic hydrolysis of the latter compound 26 gave penciclovir 4 in virtually quantitative yield. Penciclovir 4 and famciclovir 5 were prepared from 2-amino-6-[(4-chlorophenyl)sulfanyl]puri 9a in four and five steps, respectively, by procedures involving initial alkylation with 1,2-dibromoethane. The overall yields obtained were 65 and ca. 60%, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.
• AN IMPROVED PROCESS FOR THE PREPARATION OF PURINES
  申请人：Joshi Anna Ramesh

  公开号：US20050215787A1

  公开（公告）日：2005-09-29

  The present invention relates to a process for the preparation of Purines. More particularly it relates to the preparation of Purines of formula (1) wherein X is hydrogen, thioaryl; R 1 and R 2 are hydrogen or acetyl.

  本发明涉及一种制备嘌呤的方法。更具体地，它涉及制备公式（1）中的嘌呤，其中X是氢、硫芳基；R1和R2是氢或乙酰基。