5-ethoxycarbonyl-6-(4'-fluorophenyl)-4-isopropyl-2-(methylamino)pyrimidine | 147118-32-9

• 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: 5-ethoxycarbonyl-6-(4'-fluorophenyl)-4-isopropyl-2-(methylamino)pyrimidine
• 英文别名: Ethyl 4-(4-fluorophenyl)-6-isopropyl-2-methylaminopyrimidine-5-carboxylate；Ethyl 4-(4-fluorophenyl)-2-(methylamino)-6-propan-2-ylpyrimidine-5-carboxylate
• CAS: 147118-32-9
• 化学式: C₁₇H₂₀FN₃O₂
• 分子量: 317.363
• InChiKey: QWDLWJHZPSTJKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-ethoxycarbonyl-6-(4'-fluorophenyl)-4-isopropyl-2-(methylamino)pyrimidine 在 四丙基高钌酸铵 、 4 A molecular sieve 、 sodium hydride 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.5h， 生成 4-(4-氟苯基)-6-异丙基-2-[(N-甲基-N-甲磺酰)氨基]嘧啶-5-甲醛
  参考文献：
  名称：

  Synthesis and Biological Activity of Methanesulfonamide Pyrimidine- and N-Methanesulfonyl Pyrrole-Substituted 3,5-Dihydroxy-6-heptenoates, a Novel Series of HMG-CoA Reductase Inhibitors

  摘要：

  A novel series of methanesulfonamide pyrimidine- and N-methanesulfonyl pyrrole-substituted 3,5-dihydroxy-6-heptenoates were synthesized and evaluated for their ability to inhibit the enzyme HMG-CoA reductase in vitro. Monocalcium bis(+)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulfonylaminopyrimidin)-5-yl]-(3R,5S)-dihydroxy-(E)-6-heptenoate (3a,S-4522) was selected as a candidate for further evaluation. Compound 3a was approximately four times more potent than lovastatin sodium salt (in inhibiting HMG-CoA reductase in vitro (IC50 = 11 nM). Compound 3a was shown to be the most potent cholesterol biosynthesis inhibitor in this series (IC50 = 1.12 nM) in rat isolated hepatocytes; its inhibitory activity was approximately 100 times more potent than pravastatin. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00248-9
• 作为产物：
  描述：

  4-氟苯甲酰乙酸乙酯 在 叔丁基过氧化氢 、 碳酸氢钠 、 potassium carbonate 、 copper dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-ethoxycarbonyl-6-(4'-fluorophenyl)-4-isopropyl-2-(methylamino)pyrimidine
  参考文献：
  名称：

  Oxidative Dehydrogenation of Dihydropyrimidinones and Dihydropyrimidines

  摘要：

  A mild, practical procedure for oxidative dehydrogenation with catalytic amounts of a Cu salt, K2CO3, and tert-butylhydroperoxide (TBHP) as a terminal oxidant has been developed. This oxidation procedure is generally applicable to dihydropyrimidinones and most dihydropyrimidines.

  DOI：

  10.1021/ol051879w

文献信息

• Pyrimidine derivatives
  申请人：Shionogi Seiyaku Kabushiki Kaisha

  公开号：US05260440A1

  公开（公告）日：1993-11-09

  The compounds of the present invention inhibit the HMG-CoA reductase, and subsequently suppress the biosynthesis of cholesterol. And they are useful in the treatment of hypercholesterolemia, hyperlipoproteinemia, and atherosclerosis.

  本发明的化合物抑制HMG-CoA还原酶，进而抑制胆固醇的生物合成。它们在治疗高胆固醇血症、高脂蛋白血症和动脉粥样硬化方面具有用处。
• PROCESS FOR PREPARING ROSUVASTATIN CALCIUM
  申请人：Dandala Ramesh

  公开号：US20100048899A1

  公开（公告）日：2010-02-25

  The present invention relates to an improved process for preparing Rosuvastatin calcium of Formula I.

  本发明涉及一种改进的制备化学式I的罗伴他汀钙的方法。
• [EN] AN IMPROVED PROCESS FOR PREPARING PYRIMIDINE PROPENALDEHYDE<br/>[FR] PROCÉDÉ AMÉLIORÉ DE PRÉPARATION DE PYRIMIDINE PROPÉNALDÉHYDE
  申请人：AUROBINDO PHARMA LTD

  公开号：WO2010038124A1

  公开（公告）日：2010-04-08

  The present invention relates to an improved process for preparing (2E)-3-[4-(4- fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]- propenal of formula (I), which is an useful intermediate in the preparation of Rosuvastatin.

  本发明涉及一种改进的制备过程，用于制备式（I）的（2E）-3- [4-（4-氟苯基）-6-异丙基-2-（N-甲基-N-甲基磺酰基氨基）嘧啶-5-基]丙烯醛，该化合物是制备罗伐司汀的有用中间体。
• Process for preparing pyrimidine propenaldehyde
  申请人：Mallela Sambhu Prasad Sarma

  公开号：US20110178296A1

  公开（公告）日：2011-07-21

  The present invention relates to an improved process for preparing (2E)-3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-propenal of formula (I), which is an useful intermediate in the preparation of Rosuvastatin.

  本发明涉及一种改进的制备（2E）-3-[4-(4-氟苯基)-6-异丙基-2-(N-甲基-N-甲磺酰氨基)嘧啶-5-基]-丙烯醛（式（I））的方法，该方法是罗伐司汀制备中有用的中间体。
• PROCESS FOR PREPARATION OF ROSUVASTATIN CALCIUM FIELD OF THE INVENTION
  申请人：Dandala Ramesh

  公开号：US20090312547A1

  公开（公告）日：2009-12-17

  The present invention relates to an improved process for preparing (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6-enoic acid calcium of Formula (I).

  本发明涉及一种改进的制备(E)-7-[4-(4-氟苯基)-6-异丙基-2-[甲基(甲磺酰)氨基]嘧啶-5-基](3R,5S)-3,5-二羟基庚-6-烯酸钙(I式)的方法。