5-bromo-4-chloro-6-phenylpyrimidin-2-amine | 106791-93-9

• 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-bromo-4-chloro-6-phenylpyrimidin-2-amine
• CAS: 106791-93-9
• 化学式: C₁₀H₇BrClN₃
• 分子量: 284.543
• InChiKey: WPECLXUICXOZRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-4-chloro-6-phenylpyrimidin-2-amine 在 palladium(II) acetate bis(diphenylphosphino)ferrocene potassium phosphate 、 N-碘代丁二酰亚胺 作用下， 以 甲醇 、 乙二醇二甲醚 、 氯仿 、 水 为溶剂， 反应 24.5h， 生成 2-amino-5-iodo-4-methoxy-6-phenylpyrimidine
  参考文献：
  名称：

  Structural studies on bioactive compounds. Part 29

  摘要：

  The immunological agent bropirimine 5 is a tetra-substituted pyrimidine with anticancer and interferon-inducing properties. Synthetic routes to novel 5-aryl analogues of bropirimine have been developed and their potential molecular recognition properties analysed by molecular modelling methods. Sterically challenged 2-amino-5-halo-6-phenylpyrimidin-4-ones (halo = Br or I) are poor substrates for palladium catalysed Suzuki cross-coupling reactions with benzeneboronic acid because the basic conditions of the reaction converts the amphoteric pyrimidinones to their unreactive enolic forms. Palladium-mediated reductive dehalogenation of the pyrimidinone substrates effectively competes with cross-coupling. 2-Amino-5-halo-4-methoxy-6-phenylpyrimidines can be converted to a range of 5-aryl derivatives with the 5-iodopyrimidines being the most efficient substrates. Hydrolysis of the 2-amino-5-aryl-4-methoxy-6-phenylpyrimidines affords the required pyrimidin-4-ones in high yields. Semi-empirical quantum mechanical calculations show how the nature of the 5-substituent influences the equilibrium between the 1H- and 3H-tautomeric forms, and the rotational freedom about the bond connecting the 6-phenyl group and the pyrimidine ring. Both of these factors may influence the biological properties of these compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00017-1
• 作为产物：
  描述：

  2-氨基-4-氯-6-苯基嘧啶 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-bromo-4-chloro-6-phenylpyrimidin-2-amine
  参考文献：
  名称：

  三唑并嘧啶类衍生物、其制备方法及其在医药 上的应用

  摘要：

  本发明涉及三唑并嘧啶类衍生物、其制备方法及其在医药上的应用。具体而言，本发明涉及一种通式(I)所示的三唑并嘧啶类衍生物、其制备方法及含有该衍生物的药物组合物以及其作为治疗剂，特别是作为A2a受体拮抗剂的用途和在制备用于治疗通过对A2a受体的抑制而改善的病况或病症的药物中的用途，其中通式(I)的各取代基与说明书中的定义相同。

  公开号：

  CN109535161B

文献信息

• [EN] TRIAZOLE COMPOUNDS AS ADENOSINE RECEPTOR ANTAGONISTS<br/>[FR] COMPOSÉS DE TRIAZOLE UTILES EN TANT QU'ANTAGONISTES DU RÉCEPTEUR DE L'ADÉNOSINE
  申请人：ASTRAZENECA AB

  公开号：WO2021156439A1

  公开（公告）日：2021-08-12

  Described herein are triazole compounds of Formula (I): and pharmaceutically acceptable salts thereof. Methods of making and using compounds of Formula (I) are also described. Compounds of Formula (I) and pharmaceutically acceptable salts thereof can be useful as adenosine receptor antagonists, for example in the treatment of diseases or conditions mediated by the adenosine receptor, such as cancer, movement disorders, or attention disorders.

  本文描述了式（I）的三唑化合物及其药学上可接受的盐。还描述了制备和使用式（I）化合物的方法。式（I）的化合物及其药学上可接受的盐可用作腺苷受体拮抗剂，例如用于治疗由腺苷受体介导的疾病或症状，如癌症、运动障碍或注意障碍。
• 4-substituted-6-aryl-pyrimidine compounds
  申请人：The Upjohn Company

  公开号：US04795812A1

  公开（公告）日：1989-01-03

  This invention describes the synthesis and anti-neoplastic use of 4-aziridyl-5-substituted/unsubstituted 6-aryl-pyrimidine compounds of Formula IA ##STR1## as well as N'-[2-(1-aziridyl)ethyl]-6-aryl-2,4-pyrimidinediamines of Formula IB ##STR2## and 4-chloro or bromo-5-substituted/unstubstituted-6-aryl-pyrimidines.

  本发明描述了式IA中的4-氮杂环-5-取代/未取代6-芳基嘧啶化合物的合成和抗肿瘤用途，以及式IB中的N'-[2-(1-氮杂环)乙基]-6-芳基-2,4-嘧啶二胺，以及4-氯或溴-5-取代/未取代-6-芳基嘧啶。
• [EN] MODULATORS OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR<br/>[FR] MODULATEURS DU RÉGULATEUR DE LA CONDUCTANCE TRANSMEMBRANAIRE DE LA MUCOVISCIDOSE
  申请人：VERTEX PHARMA

  公开号：WO2022076627A1

  公开（公告）日：2022-04-14

  This disclosure provides modulators of Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) having the core structure:, pharmaceutical compositions containing at least one such modulator, methods of treating CFTR mediated diseases, including cystic fibrosis using such modulators and pharmaceutical compositions, combination therapies and combination pharmaceuticals employing those modulators, and processes and intermediates for making such modulators.

  本公开提供囊性纤维化跨膜传导调节因子（CFTR）的调节剂，其具有以下核心结构：，包含至少一种这样的调节剂的药物组合物，使用这样的调节剂和药物组合物治疗CFTR介导的疾病，包括囊性纤维化的方法，使用这些调节剂的组合疗法和组合药物，以及制造这些调节剂的过程和中间体。
• HETEROARYL[4,3-C]PYRIMIDINE-5-AMINE DERIVATIVE, PREPARATION METHOD THEREFOR, AND MEDICAL USES THEREOF
  申请人：Jiangsu Hengrui Medicine Co., Ltd.

  公开号：EP3575301A1

  公开（公告）日：2019-12-04

  A heteroaryl[4,3-c]pyrimidin-5-amine derivative, a preparation method therefor, and medical uses thereof. Specifically, a heteroarylo[4,3-c]pyrimidin-5-amine derivative represented by a general formula (I), a preparation method therefor, a pharmaceutical composition containing the derivative, and uses thereof as therapeutic agents, in particular, a use as a A2a receptor antagonist and A use in preparation of a medicament for treatment of conditions or symptoms that are ameliorated by inhibiting the A2a receptor; various substituent groups in the general formula (I) have the identical meanings as those in the specification.

  一种杂芳基[4,3-c]嘧啶-5-胺衍生物、其制备方法及其医疗用途。具体地说，一种由通式（I）表示的杂芳基[4,3-c]嘧啶-5-胺衍生物、其制备方法、含有该衍生物的药物组合物及其作为治疗剂的用途，特别是作为A2a受体拮抗剂的用途和制备用于治疗通过抑制A2a受体而改善的病症或症状的药物的用途；通式（I）中的各种取代基团与说明书中的取代基团具有相同的含义。
• EP3575301
  申请人：——

  公开号：——

  公开（公告）日：——