5-溴-2-嘧啶甲酸甲酯 | 89581-38-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-溴-2-嘧啶甲酸甲酯
• 中文别名: 5-溴嘧啶-2-羧酸甲酯
• 英文名称: methyl 5-bromopyrimidine-2-carboxylate
• 英文别名: methyl 5-bromo-2-pyrimidinecarboxylate；5-bromopyrimidine-2-carboxylic acid methyl ester
• CAS: 89581-38-4
• 化学式: C₆H₅BrN₂O₂
• mdl: MFCD11111606
• 分子量: 217.022
• InChiKey: XILAKTMDKMVJQV-UHFFFAOYSA-N

物化性质

• 熔点：
  149°C(lit.)
• 沸点：
  314.4±34.0 °C(Predicted)
• 密度：
  1.669
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933599090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放于惰性气体中，避免与空气接触。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 5-bromopyrimidine-2-carboxylate
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ingredient name: Methyl 5-bromopyrimidine-2-carboxylate
CAS number: 89581-38-4

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H5BrN2O2
Molecular weight: 217.0

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途
5-溴-2-嘧啶甲酸甲酯在常温常压下是白色固体粉末，具有一定的碱性，可溶于醇类有机溶剂但不溶于水。该物质的化学转化活性主要集中在其结构中的溴原子和酯基单元上。在金属催化剂的作用下，溴原子可以与金属有机试剂或有机胺类化合物发生交叉偶联反应，生成脱溴芳基化和胺化的衍生物。5-溴-2-嘧啶甲酸甲酯是一种嘧啶类衍生物，可以通过5-溴-2-嘧啶甲酸和甲醇进行酯化反应制备得到，具有丰富的化学转化活性。其结构中的溴原子在金属钯的催化作用下可与芳基硼酸类物质发生交叉偶联反应，广泛应用于嘧啶类生物活性分子的合成。

生产方法
将5-溴嘧啶-2-羧酸（3.22 g, 15.9 mmol）溶解于甲醇（50 mL），缓慢加入乙酰氯（4.0 mL, 56.3 mmol）。将反应混合物加热至回流，并保持在该状态下搅拌约15分钟。反应完成后，冷却至室温，然后在减压下浓缩反应混合物。用30 mL饱和碳酸氢钠水溶液和乙酸乙酯稀释，转移至分液漏斗中。水相用乙酸乙酯（4倍）萃取，合并所有有机层并用盐水（1倍）洗涤，分离出有机层并用无水MgS04干燥。通过过滤去除干燥剂，并将所得滤液在真空下浓缩，即可得到目标产物5-溴-2-嘧啶甲酸甲酯（2.30 g, 10.6 mmol），收率为67%，为白色固体。

反应信息

• 作为反应物：
  描述：

  5-溴-2-嘧啶甲酸甲酯 在 甲醇 、 乙醚 、 乙醇 、 氨 、 镍 、 三氯氧磷 作用下， 生成 N,N-diethylpyrimidine-2-carboxamide
  参考文献：
  名称：

  Robba, Annales de Chimie (Cachan, France), 1960, vol. <13>5, p. 351,399,402

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴嘧啶-2-羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 5-溴-2-嘧啶甲酸甲酯
  参考文献：
  名称：

  [EN] 2-ARYLSULFONAMIDO-N-ARYLACETAMIDE DERIVATIZED STAT3 INHIBITORS
  [FR] INHIBITEURS DE STAT3 DÉRIVÉS DE 2-ARYLSULFONAMIDO-N-ARYLACÉTAMIDE

  摘要：

  本公开提供了含有2-芳基磺酰胺基-N-芳基乙酰胺衍生的Stat3抑制剂及其某些药用盐的制药组合物，以及它们的使用方法。

  公开号：

  WO2018136935A1
• 作为试剂：
  描述：

  4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 、 5-溴-2-嘧啶甲酸甲酯 、 、 二氯甲烷 、 Tripotassium;phosphate 在 氩 、 N,N-二甲基甲酰胺 、 5-溴-2-嘧啶甲酸甲酯 、 乙酸乙酯 、 水 、 Brine 、 Sodium sulfate-III 、 petrol ether EtOAc 作用下， 以to afford compound 58 (40 mg, 78%) as yellow oil的产率得到methyl 5-[4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]-pyrimidine-2-carboxylate
  参考文献：
  名称：

  MANNOSE DERIVATIVES AS ANTAGONISTS OF BACTERIAL ADHESION

  摘要：

  式(I)的化合物，其中n为0、1或2，R1为芳基、杂芳基或杂环基，R2和R3为氢或规范中所述的取代基，对于预防和治疗细菌感染，特别是由大肠杆菌引起的尿路感染是有用的。

  公开号：

  US20120270824A1

文献信息

• [EN] HORMONE RECEPTOR MODULATORS FOR TREATING METABOLIC MUTAGENIC AND FIBROTIC CONDITIONS AND DISORDERS<br/>[FR] MODULATEURS DU RÉCEPTEUR HORMONAL POUR LE TRAITEMENT D'ÉTATS ET DE TROUBLES MÉTABOLIQUES MUTAGÈNES ET FIBROTIQUES
  申请人：ARDELYX INC

  公开号：WO2019055808A1

  公开（公告）日：2019-03-21

  The invention relates to activators of FXR useful in the treatment of autoimmune disorders, liver disease, intestinal disease, kidney disease, cancer, and other diseases in which FXR plays a role, having the Formula (I): wherein L1, A, X1, X2, Y1, Y2, Y3, Y4, R1, R2, and R3 are described herein.

  这项发明涉及FXR的激活剂，可用于治疗自身免疫性疾病、肝病、肠道疾病、肾脏疾病、癌症以及FXR发挥作用的其他疾病，其化学式为（I）：其中L1、A、X1、X2、Y1、Y2、Y3、Y4、R1、R2和R3如本文所述。
• [EN] BCR-ABL TYROSINE-KINASE LIGANDS CAPABLE OF DIMERIZING IN AN AQUEOUS SOLUTION, AND METHODS OF USING SAME<br/>[FR] LIGANDS DE TYROSINE-KINASE BCR-ABL CAPABLES DE SE DIMÉRISER DANS UNE SOLUTION AQUEUSE, ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：COFERON INC

  公开号：WO2015106292A1

  公开（公告）日：2015-07-16

  Described herein are monomers capable of forming a biologically useful multimer when in contact with one, two, three or more other monomers in an aqueous media. In one aspect, such monomers may be capable of binding to another monomer in an aqueous media (e.g. invivo) to form a multimer (e.g. a dimer). Contemplated monomers may include a ligand moiety, a linker element, and a connector element that joins the ligand moiety and the linker element. In an aqueous media, such contemplated monomers may join together via each linker element and may thus be capable of modulating one or more biomolecules substantially simultaneously, e.g., modulate two or more binding sites on a Bcr-Abl tyrosine kinase.

  本文描述了一种单体，当与水性介质中的另一个、两个、三个或更多其他单体接触时，能够形成生物学上有用的多聚体。在一个方面，这种单体可能能够在水性介质（例如体内）中与另一个单体结合以形成多聚体（例如二聚体）。考虑到的单体可能包括配体基团、连接元素和连接配体基团与连接元素的连接元素。在水性介质中，这些考虑到的单体可以通过每个连接元素结合在一起，因此可以同时调节一个或多个生物分子，例如，调节Bcr-Abl酪氨酸激酶上的两个或更多结合位点。
• HISTONE DEACETYLASE INHIBITOR, AND PREPARATION METHOD AND USE THEREOF
  申请人：GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD

  公开号：US20180098990A1

  公开（公告）日：2018-04-12

  A compound represented by Formula I or pharmaceutically acceptable salt thereof. The present invention relates to a 4-arylamino quinazoline hydroxamic acid compound having a histone deacetylase inhibitory activity, preparation method of the compound, pharmaceutical composition comprising the compound, and use of the compound and the pharmaceutical composition in the preparation of a histone deacetylase inhibitor medicine. The present invention aims at acquiring, via a medicine design and a synthetic technology, a series of selective histone deacetylase inhibitors having good hypotype selectivity and favorable pharmacokinetic characteristics based on optimization of an enzyme surface recognition region and connection region of 4-arylamino quinazoline, thus reducing an effect on normal tissues or cells while improving an antineoplastic activity of the normal tissues or cells.

  本发明涉及一种具有组蛋白去乙酰化酶抑制活性的4-芳氨基喹唑啉羟胺酸化合物、其制备方法、包含该化合物的药物组合物，以及该化合物和药物组合物在制备组蛋白去乙酰化酶抑制剂药物中的用途。本发明的目的是通过药物设计和合成技术，基于优化4-芳氨基喹唑啉的酶表面识别区域和连接区域，获得一系列具有良好低类型选择性和有利药代动力学特性的选择性组蛋白去乙酰化酶抑制剂，从而在提高正常组织或细胞的抗肿瘤活性的同时，减少对正常组织或细胞的影响。
• [EN] PERFLUORINATED CYCLOPROPYL FUSED 1,3-OXAZIN-2-AMINE COMPOUNDS AS BETA-SECRETASE INHIBITORS AND METHODS OF USE<br/>[FR] COMPOSÉS À BASE DE 1,3-OXAZIN-2-AMINE FUSIONNÉE AVEC DU CYCLOPROPYLE PERFLUORÉ UTILISABLES EN TANT QU'INHIBITEURS DE LA BÊTA-SÉCRÉTASE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：AMGEN INC

  公开号：WO2014138484A1

  公开（公告）日：2014-09-12

  PERFLUORINATED CYCLOPROPYL FUSED 1,3-OXAZIN-2-AMINE COMPOUNDS AS BETA-SECRETASE INHIBITORS AND METHODS OF USE ABSTRACT OF THE DISCLOSURE The present invention provides a new class of compounds useful for the modulation of beta-secretase enzyme (BACE) activity. The compounds have a general Formula I: INSERT STRUCTURE HERE} I wherein variables A4, A5, A6, A8, each of Ra, Rb, R1, R2, R3 and R7 of Formula I, independently, are defined herein. The invention also provides pharmaceutical compositions comprising the compounds, and uses of the compounds and compositions for treatment of disorders and/or conditions related to A-beta plaque formation and deposition, resulting from the biological activity of BACE. Such BACE mediated disorders include, for example, Alzheimer's Disease, cognitive deficits, cognitive impairments, schizophrenia and other central nervous system conditions. The invention further provides compounds of Formulas II and III, and sub-formula embodiments thereof, intermediates and methods for preparing compounds of the invention.

  本发明提供了一类新的化合物，用于调节β-分泌酶（BACE）活性。这些化合物具有一般的化学式I：在此插入结构} I，其中变量A4、A5、A6、A8，以及化学式I中的每个Ra、Rb、R1、R2、R3和R7，在本文中分别定义。该发明还提供了包含这些化合物的药物组合物，以及用于治疗与A-beta斑块形成和沉积相关的疾病和/或症状的化合物和组合物的用途，这些疾病和症状是由BACE的生物活性引起的。这种由BACE介导的疾病包括阿尔茨海默病、认知缺陷、认知障碍、精神分裂症和其他中枢神经系统疾病。该发明还提供了化学式II和III的化合物，以及其亚式化合物、中间体和制备本发明化合物的方法。
• Antibacterial Compounds
  申请人：BIOTA EUROPE LTD.

  公开号：US20130252938A1

  公开（公告）日：2013-09-26

  The present invention provides a compound of the following formula, salts, racemates, diastereomers, enantiomers, esters, carbamates, phosphates, sulfates, deuterated forms and prodrugs thereof. Also provided is the use of these compounds as antibacterials, compositions comprising them and processes for their manufacture.

  本发明提供了以下式的化合物，其盐、拉克酸盐、对映体、对映异构体、酯、氨基甲酸酯、磷酸酯、硫酸酯、氘代形式及其前药。 还提供了将这些化合物用作抗菌剂、包含它们的组合物以及它们的制造方法。