4-(Bromomethyl)-5-methyl-2-(methylthio)pyrimidine | 135645-55-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(Bromomethyl)-5-methyl-2-(methylthio)pyrimidine
• 英文别名: 4-(bromomethyl)-5-methyl-2-methylsulfanylpyrimidine
• CAS: 135645-55-5
• 化学式: C₇H₉BrN₂S
• 分子量: 233.132
• InChiKey: XLDYHBAZMOKJNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(Bromomethyl)-5-methyl-2-(methylthio)pyrimidine 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 二甲基亚砜 作用下， 以 四氯化碳 为溶剂， 反应 24.67h， 生成 5-(Hydroxymethyl)-2-(methylthio)-4-pyrimidinecarbaldehyde
  参考文献：
  名称：

  Highly regioselective bromination reactions of polymethylpyrimidines

  摘要：

  4,5-Dimethyl- and 4,5,6-trimethyl-substituted pyrimidines are brominated at C5-Me with NBS in CCl4 and at C4(6)-Me with bromine in acetic acid to give the corresponding bromomethyl derivatives in a high yield. The remaining methyl group(s) can also be brominated with high regioselectivity. The 2-methylthio substituent is not oxidized under these conditions.

  DOI：

  10.1021/jo00019a028
• 作为产物：
  描述：

  5-甲基-2-(甲硫基)嘧啶 在 溴 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 4-(Bromomethyl)-5-methyl-2-(methylthio)pyrimidine
  参考文献：
  名称：

  Highly regioselective bromination reactions of polymethylpyrimidines

  摘要：

  4,5-Dimethyl- and 4,5,6-trimethyl-substituted pyrimidines are brominated at C5-Me with NBS in CCl4 and at C4(6)-Me with bromine in acetic acid to give the corresponding bromomethyl derivatives in a high yield. The remaining methyl group(s) can also be brominated with high regioselectivity. The 2-methylthio substituent is not oxidized under these conditions.

  DOI：

  10.1021/jo00019a028

文献信息

• Substituted 4-phenyl pyridine compounds as non-systemic TGR5 agonists
  申请人：Ardelyx, Inc.

  公开号：US10392413B2

  公开（公告）日：2019-08-27

  The invention relates to non-systemic TGR5 agonist useful in the treatment of chemotherapy-induced diarrhea, diabetes, Type II diabetes, gestational diabetes, impaired fasting glucose, impaired glucose tolerance, insulin resistance, hyperglycemia, obesity, metabolic syndrome, ulcerative colitis, Crohn's disease, disorders associated with parenteral nutrition especially during short bowel syndrome, and irritable bowel syndrome (IBS), and other TGR5 associated diseases and disorders, having the Formula: where R1, R2, R2′, R3, R4, X1, X2, X3, X4, Q, and n are described herein.

  本发明涉及可用于治疗化疗引起的腹泻、糖尿病、II 型糖尿病、妊娠糖尿病、空腹血糖受损、糖耐量受损、胰岛素抵抗、高血糖、肥胖、代谢综合征、溃疡性结肠炎、克罗恩病、肠外营养相关疾病，尤其是短肠综合征和肠易激综合征（IBS），以及其他与 TGR5 相关的疾病和失调的非系统性 TGR5 激动剂，其配方如下： 其中 R1、R2、R2′、R3、R4、X1、X2、X3、X4、Q 和 n 如本文所述。
• SUBSTITUTED 4-PHENYL PYRIDINE COMPOUNDS AS NON-SYSTEMIC TGR5 AGONISTS
  申请人：Ardelyx, Inc.

  公开号：EP3390382A1

  公开（公告）日：2018-10-24
• [EN] SUBSTITUTED 4-PHENYL PYRIDINE COMPOUNDS AS NON-SYSTEMIC TGR5 AGONISTS<br/>[FR] UTILISATION DE COMPOSÉS 4-PHÉNYL PYRIDINE SUBSTITUÉS EN TANT QU'AGONISTES NON SYSTÉMIQUES DU TGR5
  申请人：ARDELYX INC

  公开号：WO2017106818A1

  公开（公告）日：2017-06-22

  The invention relates to non-systemic TGR5 agonist useful in the treatment of chemotherapy-induced diarrhea, diabetes, Type II diabetes, gestational diabetes, impaired fasting glucose, impaired glucose tolerance, insulin resistance, hyperglycemia, obesity, metabolic syndrome, ulcerative colitis, Crohn's disease, disorders associated with parenteral nutrition especially during short bowel syndrome, and irritable bowel syndrome (IBS), and other TGR5 associated diseases and disorders, having the Formula: (I'), where R1, R2, R2', R3, R4, X1, X2, X3, X4, Q, and n are described herein.
• [EN] AMINO-PYRIMIDINE CYCLO-AMIDES<br/>[FR] CYCLOAMIDES D'AMINO-PYRIMIDINE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2021249904A2

  公开（公告）日：2021-12-16

  The invention provides novel compounds having the general formula (I) wherein R1, R2, R3 and n are as defined herein, compositions including the compounds and methods of using the compounds.
• Highly regioselective bromination reactions of polymethylpyrimidines
  作者：Lucjan Strekowski、Roman L. Wydra、Lubomir Janda、Donald B. Harden

  DOI：10.1021/jo00019a028

  日期：1991.9

  4,5-Dimethyl- and 4,5,6-trimethyl-substituted pyrimidines are brominated at C5-Me with NBS in CCl4 and at C4(6)-Me with bromine in acetic acid to give the corresponding bromomethyl derivatives in a high yield. The remaining methyl group(s) can also be brominated with high regioselectivity. The 2-methylthio substituent is not oxidized under these conditions.