5-ethoxycarbonyl-6-(4'-fluorophenyl)-4-isopropyl-2-(methylamino)-1,4-dihydropyrimidine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 5-ethoxycarbonyl-6-(4'-fluorophenyl)-4-isopropyl-2-(methylamino)-1,4-dihydropyrimidine
• 英文别名: Ethyl 4-(4-fluorophenyl)-6-isopropyl-2-methylamino-1,6-dihydropyrimidine-5-carboxylate；ethyl 6-(4-fluorophenyl)-2-methylimino-4-propan-2-yl-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₇H₂₂FN₃O₂
• 分子量: 319.379
• InChiKey: JTXOTDJQFWHXEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  62.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-ethoxycarbonyl-6-(4'-fluorophenyl)-4-isopropyl-2-(methylamino)-1,4-dihydropyrimidine 在 叔丁基过氧化氢 、 potassium carbonate 、 copper dichloride 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到5-ethoxycarbonyl-6-(4'-fluorophenyl)-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
• 作为产物：
  描述：

  甲胍 、 4-氟苯甲酰乙酸乙酯 、 异丁醛 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到5-ethoxycarbonyl-6-(4'-fluorophenyl)-4-isopropyl-2-(methylamino)-1,4-dihydropyrimidine
  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

• Process for the Preparation of Pyrimidine Compounds
  申请人：Newton Lee

  公开号：US20060052604A1

  公开（公告）日：2006-03-09

  A process for the preparation of a compound of Formula (I) and intermediates useful therein are provided. The process comprises reacting a compound of formula R 1 —CO—CH 2 -E with a compound of formula R 2 —CHX 1 X 2 in the presence of a compound of formula R 3 R 4 N—C(═NH)NH 2 and a catalyst, thereby to form a dihydropyrimidine; and oxidising the dihydropyrimidine to form the compound of Formula ( 1 ). R 1 is H or an alkyl group; R 2 is H, an alkyl or aryl group; R 3 and R 4 are each independently H, alkyl or aryl, or R 3 and R 4 are linked to form, together with the nitrogen to which they are attached to form a 5 to 7 membered heterocyclic ring; E is H, an unsubstituted alkyl group, and aryl group or an electron withdrawing group; and X 1 and X 2 are each independently leaving groups, or X 1 and X 2 together represent ═O.

  提供了制备式（I）化合物及其有用中间体的方法。该方法包括在化合物R1—CO—CH2-E与化合物R2—CHX1X2在化合物R3R4N—C（═NH）NH2和催化剂的存在下反应，从而形成二氢嘧啶；然后氧化二氢嘧啶以形成式（1）化合物。其中，R1为H或烷基；R2为H、烷基或芳基；R3和R4各自独立地为H、烷基或芳基，或R3和R4连接在一起，与它们附着的氮一起形成5至7个成员的杂环环；E为H、未取代的烷基、芳基或电子吸引基团；X1和X2各自独立地为离去基，或X1和X2一起表示═O。
• PROCESS FOR THE PREPARATION OF PYRIMIDINE COMPOUNDS
  申请人：NEWTON Lee

  公开号：US20090264654A1

  公开（公告）日：2009-10-22

  A process for the preparation of a compound of Formula (1) and intermediates useful therein are provided. The process comprises reacting a compound of formula R 1 —CO—CH 2 -E with a compound of formula R 2 —CHX 1 X 2 in the presence of a compound of formula R 3 R 4 N—C(═NH)NH 2 and a catalyst, thereby to form a dihydropyrimidine; and oxidising the dihydropyrimidine to form the compound of Formula (I). R 1 is H or an alkyl group; R 2 is H, an alkyl or aryl group; R 3 and R 4 are each independently H, alkyl or aryl, or R 3 and R 4 are linked to form, together with the nitrogen to which they are attached to form a 5 to 7 membered heterocyclic ring; E is H, an unsubstituted alkyl group, an aryl group or an electron withdrawing group; and X 1 and X 2 are each independently leaving groups, or X 1 and X 2 together represent ═O.

  提供了一种制备式（1）化合物及其有用中间体的方法。该方法包括在化合物R1—CO—CH2-E和化合物R2—CHX1X2的存在下，与化合物R3R4N—C（═NH）NH2和催化剂反应，从而形成二氢嘧啶；然后氧化二氢嘧啶，形成式（I）化合物。其中，R1为H或烷基；R2为H、烷基或芳基；R3和R4各自独立地为H、烷基或芳基，或R3和R4连在一起，与它们所连接的氮形成5至7成员杂环环；E为H、未取代的烷基、芳基或电子吸引基团；X1和X2各自独立为离去基团，或X1和X2一起代表═O。
• Process for the preparation of pyrimidine compounds
  申请人：AstraZeneca UK Limited

  公开号：US08273878B2

  公开（公告）日：2012-09-25

  A process for the preparation of a compound of Formula (1) and intermediates useful therein are provided. The process comprises reacting a compound of formula R1—CO—CH2-E with a compound of formula R2—CHX1X2 in the presence of a compound of formula R3R4N—C(═NH)NH2 and a catalyst, thereby to form a dihydropyrimidine; and oxidizing the dihydropyrimidine to form the compound of Formula (I). R1 is H or an alkyl group; R2 is H, an alkyl or aryl group; R3 and R4 are each independently H, alkyl or aryl, or R3 and R4 are linked to form, together with the nitrogen to which they are attached to form a 5 to 7 membered heterocyclic ring; E is H, an unsubstituted alkyl group, an aryl group or an electron withdrawing group; and X1 and X2 are each independently leaving groups, or X1 and X2 together represent ═O.

  提供一种制备化合物式（1）及其中间体的方法。该方法包括在化合物R1-CO-CH2-E和化合物R2-CHX1X2的存在下，与化合物R3R4N-C（═NH）NH2和催化剂反应，形成二氢嘧啶；然后氧化二氢嘧啶，形成化合物式（I）。其中，R1为H或烷基；R2为H，烷基或芳基；R3和R4各自独立地为H，烷基或芳基，或R3和R4连接在一起，与它们所附着的氮一起形成5至7成员杂环环；E为H，未取代的烷基，芳基或电子提取基团；X1和X2各自独立地为离去基团，或X1和X2一起表示═O。
• Compounds and Processes
  申请人：AstraZeneca UK Limited

  公开号：EP2088142A2

  公开（公告）日：2009-08-12

  Intermediates of formula and processes for their preparation are provided. The process comprises reacting a compound of formula R1-CO-CH2-E with a compound of formula R2-CHX1X2 in the presence of a compound of formula R3R4N-C(=NH)NH2 and a catalyst. R1 is H or an alkyl group; R2 is H, an alkyl or aryl group; R3 and R4 are each independently H, alkyl or aryl, or R3 and R4 are linked to form, together with the nitrogen to which they are attached to form a 5 to 7 membered heterocyclic ring; E is H, an unsubstituted alkyl group, an aryl group or an electron withdrawing group; and X1 and X2 are each independently leaving groups, or X1 and X2 together represent =O.

  式的中间体 及其制备工艺。该工艺包括在式 R3R4N-C(=NH)NH2 化合物和催化剂存在下，使式 R1-CO-CH2-E 化合物与式 R2-CHX1X2 化合物反应。R1是H或烷基；R2是H、烷基或芳基；R3和R4各自独立地是H、烷基或芳基，或R3和R4相连，与它们所连接的氮一起形成5至7个成员的杂环；E是H、未取代的烷基、芳基或退电子基团；X1和X2各自独立地是离去基团，或X1和X2一起代表＝O。
• [EN] PROCESS FOR THE PREPARATION OF PYRIMIDINE COMPOUNDS<br/>[FR] COMPOSES ET PROCEDES
  申请人：ASTRAZENECA UK LTD

  公开号：WO2004054986A3

  公开（公告）日：2004-12-02