4-(4-Benzyloxy-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester

• 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-(4-Benzyloxy-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester
• 英文别名: Methyl 4-[4-(benzyloxy)phenyl]-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；methyl 6-methyl-4-(4-phenylmethoxyphenyl)-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₂₀H₂₀N₂O₃S
• 分子量: 368.456
• InChiKey: YNUFUDUTDPPBOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-Benzyloxy-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester 在 1,10-菲罗啉 、 噻吩-2-甲酸亚铜(I) 、 氨 、 palladium diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以83%的产率得到methyl 2-amino-4-(4-benzyloxyphenyl)-6-methylpyrimidine-5-carboxylate
  参考文献：
  名称：

  Pd/Cu-assisted C–S activation and N–H insertion: highly versatile synthesis of 2-aminopyrimidines from 3,4-dihydropyrimidine-2(1H)-thiones

  摘要：

  A method for the synthesis of 2-aminopyrimidines from readily available 3,4-dihydropyrimidine-2(1H)-thiones via a palladium-assisted C-S activation and N-H insertion reaction is developed. The process provides an access to a variety of highly diverse 2-aryl(alkyl)-aminopyrimidine adducts in good yields.

  DOI：

  10.1007/s10593-018-2276-0
• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 乙酰乙酸甲酯 、 硫脲 在 calcium chloride 作用下， 反应 0.03h， 以85%的产率得到4-(4-Benzyloxy-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Misra, Anup Kumar; Agnihotri, Geetanjali; Madhusudan, Soni Kamlesh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 9, p. 2018 - 2020

  摘要：

  DOI：

文献信息

• A Simple and Efficient One-Pot Synthesis of Multifunctional 5-Aryl-<i>5H</i>-thiazolo[3,2-a]pyrimidines
  作者：Seerat Fatima、Anindra Sharma、Rahul Sharma、Rama P. Tripathi

  DOI：10.1002/jhet.831

  日期：2012.5

  One‐pot economical and efficient synthesis of multifunctional 5H‐thiazolo[3,2‐a]pyrimidines by the reaction of 4‐aryl dihydrothiopyrimidines with propargyl bromide in the presence of inorganic base has been reported in very short time.

  据报道，在很短的时间内，可以通过4-芳基二氢硫代嘧啶与炔丙基溴的反应，一锅经济，高效地合成多功能5H-噻唑并[3,2-a]嘧啶。
• [EN] 2-THIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE DERIVATIVES<br/>[FR] DERIVES DE 2-THIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE
  申请人：ONO PHARMACEUTICAL CO

  公开号：WO2002066443A2

  公开（公告）日：2002-08-29

  The present invention is related to: (1) neutral sphingomyelinase inhibitors containing 2-thioxo 1,2,3,4-tetrahydropyrimidine derivatives of the formula (I): wherein all of the symbols have the same meanings as described hereinbefore, or a non-toxic salt thereof, a hydrate thereof, or a prodrug thereof as active ingredient, (2) novel 2-thioxo-1,2,3,4-tetrahydropyrimidine derivatives of the formula (I): wherein all of the symbols have the same meanings as described hereinbefore, or a non-toxic salt thereof, a hydrate thereof, or a prodrug thereof, (3) some novel specific compounds, and (4) process for the preparation of the compounds of the formula (Ia), or a prodrug thereof. The compounds of the present invention of the formulae (I) and (Ia) are neutral sphingomyelinase inhibitors and therefore are useful for the treatment and/or prevention of arteriosclerosis, cerebral ischemia, cardiac ischemia, lung injury, renal injury, GVHD (graft versus host diseases), transplant rejection, HIV, etc.
• Misra, Anup Kumar; Agnihotri, Geetanjali; Madhusudan, Soni Kamlesh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 9, p. 2018 - 2020
  作者：Misra, Anup Kumar、Agnihotri, Geetanjali、Madhusudan, Soni Kamlesh

  DOI：——

  日期：——
• Pd/Cu-assisted C–S activation and N–H insertion: highly versatile synthesis of 2-aminopyrimidines from 3,4-dihydropyrimidine-2(1H)-thiones
  作者：Hina Mathur、Mohammed Shahrukh Khan Zai、Poonam Khandelwal、Neetu Kumari、Ved Prakash Verma、Dinesh Kumar Yadav

  DOI：10.1007/s10593-018-2276-0

  日期：2018.3

  A method for the synthesis of 2-aminopyrimidines from readily available 3,4-dihydropyrimidine-2(1H)-thiones via a palladium-assisted C-S activation and N-H insertion reaction is developed. The process provides an access to a variety of highly diverse 2-aryl(alkyl)-aminopyrimidine adducts in good yields.