2-氨基-4-溴-6-甲基嘧啶 | 5734-71-4

• 物质功能分类: 医药中间体 - 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: 2-氨基-4-溴-6-甲基嘧啶
• 英文名称: 4-bromo-6-methylpyrimidin-2-amine
• CAS: 5734-71-4
• 化学式: C₅H₆BrN₃
• 分子量: 188.027
• InChiKey: QOGNMKRPXKNSPZ-UHFFFAOYSA-N

物化性质

• 熔点：
  153 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  347.3±34.0 °C(Predicted)
• 密度：
  1.699±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090
• 储存条件：
  存放在2-8°C的环境中，避免光照，并保持在惰性气体中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-4-bromo-6-methylpyrimidine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Amino-4-bromo-6-methylpyrimidine
CAS number: 5734-71-4

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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: C5H6BrN3
Molecular weight: 188.0

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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

外观

固体

用途

2-氨基-4-溴-6-甲基嘧啶主要用于合成双磷酸盐。此外，它也在杂环膦酸盐和药物合成中发挥重要作用。

反应信息

• 作为反应物：
  描述：

  2-氨基-4-溴-6-甲基嘧啶 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  发现对单子叶草具有强除草活性的邻位烷氧基取代的新型磺酰脲类化合物

  摘要：

  在本研究中，我们设计并合成了一系列 42 种在苯环上具有邻烷氧基取代的新型磺酰脲类化合物，并评估了它们的除草活性。一些目标化合物对单子叶杂草种类显示出优异的除草活性。当以 7.5 g ha –1、6–11施用时，对稗草 ( Echinochloa crus-galli ) 和马唐草 ( Digitaria sanguinalis ) 的除草活性比商业乙酰羟酸合酶 (AHAS；EC 2.2.1.6) 抑制剂三嘧磺隆、五氟磺草胺、芽前和芽后条件下的烟嘧磺隆。6–11以这种超低剂量对花生进行芽后施用是安全的，这表明它可以被认为是花生田的潜在除草剂候选物。尽管6-11和三嘧磺隆具有相似的化学结构并且对植物 AHAS 的K i值接近，但从 DFT 计算中观察到它们的 LUMO 图之间存在显着差异，这可能是导致它们对单子叶杂草种类不同行为的一个可能因素.

  DOI：

  10.1021/acs.jafc.1c02081
• 作为产物：
  描述：

  2-氨基-4-羟基-6-甲基嘧啶 在 三溴氧磷 作用下， 生成 2-氨基-4-溴-6-甲基嘧啶
  参考文献：
  名称：

  氢溴酸磷作为溴化剂；溴嘧啶。

  摘要：

  DOI：

  10.1021/jo01166a013

文献信息

• <i>N</i>-Leucinyl Benzenesulfonamides as Structurally Simplified Leucyl-tRNA Synthetase Inhibitors
  作者：Michael H. Charlton、Rihards Aleksis、Adélaïde Saint-Leger、Arya Gupta、Einars Loza、Lluís Ribas de Pouplana、Ilze Kaula、Daina Gustina、Marina Madre、Daina Lola、Kristaps Jaudzems、Grace Edmund、Christopher P. Randall、Louise Kime、Alex J. O’Neill、Wil Goessens、Aigars Jirgensons、Paul W. Finn

  DOI：10.1021/acsmedchemlett.7b00374

  日期：2018.2.8

  Enzymatic assays revealed that N-leucinyl benzenesulfonamides display remarkable selectivity for E. coli leucyl-tRNA synthetase compared to S. aureus and human orthologues. The simplest analogue of the series, N-leucinyl benzenesulfonamide (R = H), showed the highest affinity against E. coli leucyl-tRNA synthetase and also exhibited antibacterial activity against Gram-negative pathogens (the best MIC = 8 μg/mL

  已发现N-亮氨酰苯磺酰胺是一类新型的大肠杆菌亮氨酰-tRNA合成酶的有效抑制剂。抑制剂与酶的结合通过使用等温滴定热法来测量。这提供了关于焓和熵对结合的贡献的信息，这些信息与对接研究一起用于结构-活性关系分析。酶法测定显示，与金黄色葡萄球菌和人类直系同源物相比，N-亮氨酰苯磺酰胺对大肠杆菌亮氨酰-tRNA合成酶显示出显着的选择性。该系列中最简单的类似物N-亮氨酰苯磺酰胺（R = H）对大肠杆菌表现出最高的亲和力亮氨酰tRNA合成酶，并且还显示出对革兰氏阴性病原体的抗菌活性（最佳MIC = 8μg/ mL，大肠杆菌ATCC 25922），这使其成为抗菌药物发现的有希望的模板。
• [EN] SUBSTITUTED OXOISOINDOLINE COMPOUNDS FOR THE TREATMENT OF CANCER<br/>[FR] COMPOSÉS D'OXOISOINDOLINE SUBSTITUÉS POUR LE TRAITEMENT DU CANCER
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2021194914A1

  公开（公告）日：2021-09-30

  Disclosed are compounds of Formula (I) or a salt thereof, wherein Ring A is a carbon-linked ring; and Ring A, R1, and n are defined herein. Also disclosed are methods of using such compounds to inhibit Helios protein, and pharmaceutical compositions comprising such compounds. These compounds are useful in the treatment of viral infections and proliferative disorders, such as cancer.

  揭示了化合物的结构式（I）或其盐，其中环A是一个碳链环；环A，R1和n在此处有定义。还揭示了使用这些化合物抑制Helios蛋白的方法，以及包含这些化合物的药物组合物。这些化合物在治疗病毒感染和增生性疾病（如癌症）方面具有用途。
• Amberlyst-15 catalyzed synthesis of alkyl/aryl/heterocyclic phosphonates
  作者：U.M. Rao Kunda、V.N. Reddy Mudumala、C.S. Reddy Gangireddy、B.R. Nemallapudi、K.N. Sandip、S.R. Cirandur

  DOI：10.1016/j.cclet.2011.01.033

  日期：2011.8

  A novel and efficient procedure for the synthesis of alkyl phosphonates through one pot condensation of alkyl halide and tri alkyl/aryl phosphite in the presence of amberlyst-15 as catalyst under solvent free conditions was applied. It demonstrated several advantages such as good yields of products, simple operation, convenient separation and inexpensive catalyst.

  在无溶剂条件下，采用琥珀酰-15作为催化剂，通过烷基卤化物和亚磷酸三烷基酯/亚芳基酯的一锅缩合，合成了一种新颖而有效的合成膦酸烷基酯的方法。它显示出许多优点，例如产物的产率高，操作简单，分离方便和催化剂便宜。
• Chemical synthesis, biological activities, and molecular simulations of novel sulfonylurea compounds bearing <i>ortho</i> ‐alkoxy substitutions
  作者：Ming‐Hao Shang、Kai Zhang、Jia‐Shuang Zhang、Cong‐Wei Niu、Yong‐Hong Li、Fu‐Hang Song、Jian‐Guo Wang

  DOI：10.1111/cbdd.14114

  日期：2022.10

  assay. Among the target compounds, 6e showed desirable antifungal activity against Candida albicans standard isolate sc5314 with minimum inhibition concentration (MIC) of 0.39 mg/L (0.98 μM) after 24 h, and 6a demonstrated promising pre-emergence herbicidal activity against Echinochloacrus-galli at 30 g/ha dosage. Representative compounds 6a, 6e, and 6i showed no cell cytotoxicity even at 40 mg/L concentration

  化学合成了一系列51种苯环上具有邻位烷氧基取代基的新型磺酰脲类化合物，并对其进行了光谱表征。使用对来自真菌或植物来源的乙酰羟酸合酶 (AHAS; EC 2.2.1.6) 的酶抑制以及基于细胞的抗真菌测定和温室盆栽除草测定来评估目标化合物的生物活性。在目标化合物中，6e对白色念珠菌标准分离株 sc5314表现出理想的抗真菌活性，24 小时后最小抑制浓度 (MIC) 为 0.39 mg/L (0.98 μM)，6a对EChinochloacrus-galli表现出有希望的芽前除草活性剂量为 30 克/公顷。代表性化合物6a、6e和6i即使在 40 mg/L 浓度下也没有显示出细胞毒性。理论 DFT 计算表明应考虑 HOMO 图以了解结构-活性关系。因此，本研究为进一步发现新型抗真菌剂或选择性除草剂提供了有用的信息。
• [EN] BRIDGED COMPOUNDS AS KRAS G12D INHIBITOR AND DEGRADER AND THE USE THEREOF<br/>[FR] COMPOSÉS PONTÉS EN TANT QU'INHIBITEUR ET DÉGRADEUR DE KRAS G12D ET LEUR UTILISATION
  申请人：BEIGENE LTD

  公开号：WO2022148422A1

  公开（公告）日：2022-07-14

  Provided herein are Bridged Compounds having the following structures: (I) wherein R1a, R1b, R1c, R1d, R2a, R2b, R2c, R2d, R3a, R3b, R3c, R3d, R4, R5, R6, R7, R8, m1, m2, m3, n2, n3, n4, q, X1, X2, Y1, Y2, L1and ring A are as defined herein, compositions comprising an effective amount of a Bridged Compound, and methods for treating or preventing various diseases, e.g., pancreatic cancer, or a condition treatable or preventable by inhibition of the function of KRAS protein. In another aspect, a Bridged Compound is useful for treating or preventing a condition treatable or preventable by inhibition of the function of KRAS protein with G12D mutation. In another aspect, a Bridged Compound is useful for treating or preventing a condition treatable or preventable by inhibition of a RAS/MAPK pathway.

  本文提供了具有以下结构的桥接化合物：（I），其中R1a，R1b，R1c，R1d，R2a，R2b，R2c，R2d，R3a，R3b，R3c，R3d，R4，R5，R6，R7，R8，m1，m2，m3，n2，n3，n4，q，X1，X2，Y1，Y2，L1和环A的定义如本文所述，包含有效量的桥接化合物的组合物，以及用于治疗或预防各种疾病的方法，例如胰腺癌或可通过抑制KRAS蛋白功能来治疗或预防的疾病。在另一个方面，桥接化合物可用于治疗或预防可通过抑制具有G12D突变的KRAS蛋白功能来治疗或预防的疾病。在另一个方面，桥接化合物可用于治疗或预防可通过抑制RAS / MAPK途径来治疗或预防的疾病。