2-甲基-5-溴嘧啶-4-羧酸 | 100707-39-9

• 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: 2-甲基-5-溴嘧啶-4-羧酸
• 中文别名: 5-溴-2-甲基嘧啶-4-甲酸；2-甲基-5-溴嘧啶-4-甲酸；5-溴-2-甲基-4-嘧啶甲酸；2-甲基-5-溴-4-嘧啶羧酸
• 英文名称: 5-bromo-2-methylpyrimidine-4-carboxylic acid
• CAS: 100707-39-9
• 化学式: C₆H₅BrN₂O₂
• mdl: MFCD00466678
• 分子量: 217.022
• InChiKey: MDERWSRHRJUWNS-UHFFFAOYSA-N

物化性质

• 熔点：
  172-173 °C (decomp)(Solv: methanol (67-56-1))
• 沸点：
  335.2±27.0 °C(Predicted)
• 密度：
  1.795±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  63.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933599090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Methyl-5-bromopyrimidine-4-carboxylic acid
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-Methyl-5-bromopyrimidine-4-carboxylic acid
CAS number: 100707-39-9

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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.
Store in closed vessels.
Storage:

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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
No data
Melting point:
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

2-甲基-5-溴嘧啶-4-羧酸是一种用于有机合成和其他化学过程的研究化学品。由于嘧啶类化合物广泛存在于人体和生物体内，这类化合物一直受到医药和农药界的重视。

制备

该化合物可以通过两种方法制备：

1. 以2,4-二甲基-5-溴嘧啶为起始物料，在碱性条件下，经高锰酸钾氧化后得到目标化合物2-甲基-5-溴嘧啶-4-羧酸[1]。

2. 以3,4-二溴-5-羟基呋喃-2(5H)-酮为起始物料，与盐酸乙脒成环制备得到2-甲基-5-溴嘧啶-4-羧酸。

2-甲基-5-溴嘧啶-4-羧酸的合成反应式如下图所示： 

反应信息

• 作为反应物：
  描述：

  2-甲基-5-溴嘧啶-4-羧酸 在 四(三苯基膦)钯 sodium hydride 、 sodium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 2-Methyl-5-phenyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide
  参考文献：
  名称：

  5-phenyl-pyrimidine derivatives

  摘要：

  描述了一般公式的化合物：其中R1是氢或卤素；R2是氢、卤素、低烷基或低烷氧基；R3是卤素、三氟甲基、低烷氧基或低烷基；R4/R4′分别是氢或低烷基；R5是低烷基、低烷氧基、氨基、羟基、羟基-低烷基、—(CH2)n-哌嗪基，可选地被低烷基取代，—(CH2)n-吗啉基，—(CH2)n+1-咪唑基，—O—(CH2)n+1-吗啉基，—O—(CH2)n+1-哌啶基，低烷基硫基，低烷基磺酰基，苄氨基，—NH—(CH2)n+1N(R4″)2，—(CH2)n—NH—(CH2)n+1N(R4″)2，—(CH2)n+1N(R4″)2，或—O—(CH2)n+1N(R4″)2，其中R4″是氢或低烷基；R6是氢；R2和R6或R1和R6可以共同为—CH2CH—CH2CH—，其中R2和R6或R1和R6，分别与它们连接的两个碳环原子形成融合环，但R1的n为1；n独立地为0-2；X为—C(O)N(R4″)—或—N(R4″)C(O)—；以及其药学上可接受的酸盐。

  公开号：

  US06756380B1
• 作为产物：
  描述：

  粘溴酸 、 盐酸乙脒 在 sodium ethanolate 作用下， 生成 2-甲基-5-溴嘧啶-4-羧酸
  参考文献：
  名称：

  Budesinsky, Collection of Czechoslovak Chemical Communications, 1949, vol. 14, p. 223,228

  摘要：

  DOI：

文献信息

• [EN] FUSED IMIDAZOLE DERIVATIVES AS IL-17 MODULATORS<br/>[FR] DÉRIVÉS D'IMIDAZOLE FUSIONNÉS UTILISÉS EN TANT QU'INHIBITEURS D'IL-17
  申请人：UCB BIOPHARMA SPRL

  公开号：WO2019138017A1

  公开（公告）日：2019-07-18

  A series of substituted fused bicyclic imidazole derivatives, including benzimidazole derivatives and analogues thereof, being potent modulators of human IL-17 activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including inflammatory and autoimmune disorders.

  一系列替代的融合双环咪唑衍生物，包括苯并咪唑衍生物及其类似物，作为强效的人IL-17活性调节剂，因此在治疗和/或预防各种人类疾病，包括炎症性和自身免疫性疾病方面具有益处。
• TREATMENT OF CANCERS HAVING K-RAS MUTATIONS
  申请人：Curis, Inc.

  公开号：US20130102595A1

  公开（公告）日：2013-04-25

  The present invention provides a method of treating a cancer associated with a K-ras mutation in a subject in need thereof. The method comprises the steps of: (1) identifying a subject with a cancer associated with a K-ras mutation; and (2) administering to the subject (i) an inhibitor of PI3 kinase and (ii) an HDAC inhibitor, wherein the PI3 kinase inhibitor and the HDAC inhibitor are administered in amounts which together are therapeutically effective.

  本发明提供了一种治疗与K-ras突变相关的癌症的方法，适用于需要该方法的受试者。该方法包括以下步骤：（1）识别患有与K-ras突变相关的癌症的受试者；和（2）向受试者施用（i）PI3激酶抑制剂和（ii）HDAC抑制剂，其中PI3激酶抑制剂和HDAC抑制剂以联合治疗有效的剂量进行施用。
• [EN] TREATMENT OF CANCERS HAVING K-RAS MUTATIONS<br/>[FR] TRAITEMENT DE CANCERS PRÉSENTANT DES MUTATIONS K-RAS
  申请人：CURIS INC

  公开号：WO2011130628A1

  公开（公告）日：2011-10-20

  The present invention provides a method of treating a cancer associated with a K- ras mutation in a subject in need thereof. The method comprises the steps of (1) identifying a subject with a cancer associated with a K-ras mutation; and (2) adminsiterign to the subject (i) an inhibitor of PI3 kinase and (ii) an HDAC inhibitor, wherein the PI3 kinase inhibitor and the HDAC inhibitor are administered in amounts which together are therapeutically effective.

  本发明提供了一种治疗与K-ras突变相关的癌症的方法，适用于需要该方法的受试者。该方法包括以下步骤：(1) 鉴定患有与K-ras突变相关的癌症的受试者；和 (2) 给予该受试者 (i) PI3激酶抑制剂和 (ii) HDAC抑制剂，其中PI3激酶抑制剂和HDAC抑制剂以治疗有效的剂量一起给予。
• [EN] CYCLIC INHIBITORS OF 11ß-HYDROXYSTERIOD DEHYDROGENASE 1<br/>[FR] INHIBITEURS CYCLIQUES DE LA 11?-HYDROXYSTÉROÏDE DÉSHYDROGÉNASE 1
  申请人：VITAE PHARMACEUTICALS INC

  公开号：WO2009017664A1

  公开（公告）日：2009-02-05

  This invention relates to novel compounds of the Formula (I), (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih); (Ii); (Ij), (Ik), (II) pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful for the therapeutic treatment of diseases associated with the modulation or inhibition of 11 β-HSD1 in mammals. The invention further relates to pharmaceutical compositions of the novel compounds and methods for their use in the reduction or control of the production of cortisol in a cell or the inhibition of the conversion of cortisone to cortisol in a cell.

  本发明涉及式(I)、(Ia)、(Ib)、(Ic)、(Id)、(Ie)、(If)、(Ig)、(Ih)；(Ii)；(Ij)，(Ik)，(II)的新颖化合物，其药用可接受的盐以及药物组合物，这些化合物对于治疗与调节或抑制哺乳动物中的11β-HSD1相关的疾病是有用的。本发明进一步涉及新颖化合物的药物组合物及其在减少或控制细胞中皮质醇的产生或抑制细胞中将可的松转化为皮质醇的方法。
• NITROGEN CONTAINING HETEROARYL COMPOUNDS
  申请人：Bleicher Konrad

  公开号：US20110306589A1

  公开（公告）日：2011-12-15

  The invention is concerned with novel nitrogen-containing heteroaryl compounds of formula (I) wherein A 1 , A 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds inhibit PDE10A and can be used as therapeutics.

  这项发明涉及一种新颖的含氮杂环芳基化合物，其化学式为（I），其中A1、A2、R1、R2、R3、R4、R5和R6如描述和索赔中所定义，并且其生理上可接受的盐和酯。这些化合物抑制PDE10A并可用作治疗药物。