4-羟基-5-氰基嘧啶 | 4774-34-9

• 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: 4-羟基-5-氰基嘧啶
• 中文别名: 5-氰基-4-羟基嘧啶
• 英文名称: 3,4-Dihydro-4-oxopyrimidin-5-carbonitril
• 英文别名: 6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile；6-oxo-1H-pyrimidine-5-carbonitrile
• CAS: 4774-34-9
• 化学式: C₅H₃N₃O
• mdl: MFCD00087111
• 分子量: 121.098
• InChiKey: SVOQOFSQLVVHKQ-UHFFFAOYSA-N

物化性质

• 熔点：
  244-249°C
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R22,R41
• WGK Germany：
  3
• 海关编码：
  2933599090
• 危险标志：
  GHS05,GHS07
• 危险性描述：
  H302,H318
• 危险性防范说明：
  P280,P305 + P351 + P338

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Hydroxypyrimidine-5-carbonitrile
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H318: Causes serious eye damage
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

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-Hydroxypyrimidine-5-carbonitrile
CAS number: 4774-34-9

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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
This product should be handled only by, or under the close supervision of, those properly qualified
Handling:
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.

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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: C5H3N3O
Molecular weight: 121.1

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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.

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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

反应信息

• 作为反应物：
  描述：

  4-羟基-5-氰基嘧啶 在 氨 、 氢气 作用下， 以 甲醇 为溶剂， 生成 5-(aminomethyl)-1H-pyrimidin-6-one
  参考文献：
  名称：

  Zeste同源2（EZH2）增强剂和Zeste同源1（EZH1）抑制剂增强剂的构效关系研究。

  摘要：

  EZH2或EZH1（zeste同源物2或1的增强剂）是多梳抑制复合物2（PRC2）的催化亚基，可催化组蛋白H3赖氨酸27（H3K27）的甲基化。PRC2的过度活跃和/或H3K27的过度三甲基化与许多人类癌症相关，因此抑制PRC2的复合体已成为一种有前途的治疗方法。最近的研究表明，EZH2和EZH1在功能上不是多余的，抑制EZH2和EZH1两者对于阻止某些癌症（如混合谱系白血病（MLL）重排的白血病）的进展是必要的。尽管EZH2抑制剂的发现取得了重大进展，但尚未进行系统的结构-活性关系（SAR）研究来研究EZH2和EZH1抑制剂之间的选择性。这里，5）研究结构变化对EZH2和EZH1抑制和选择性的影响。

  DOI：

  10.1021/acs.jmedchem.6b00855
• 作为产物：
  描述：

  醋酸甲脒 、 2-氰基-3-乙氧基丙烯酸乙酯 在 sodium methylate 作用下， 以 乙醇 为溶剂， 以75%的产率得到4-羟基-5-氰基嘧啶
  参考文献：
  名称：

  一种医药中间体4-氯-5-氰基嘧啶制备方法

  摘要：

  本发明公开了一种医药中间体4‑氯‑5氰基嘧啶制备方法。本发明的方法是将式(II)所示化合物2‑氰基‑3‑乙氧基丙烯酸乙酯在质子性溶剂中与式(III)所示化合物醋酸甲脒在醇钠存在下发生合环反应，得式(IV)所示的化合物，再与五氯化磷、三氯氧磷、二氯亚砜或三氯化磷中的任意一种或两种或两种以上进行氯化反应，制得式(I)所示的化合物4‑氯‑5氰基嘧啶。本发明的制备方法具有如下有益效果：合成路线短，合成方便，收率高，原料毒性小，环境污染较低，具备高纯度、高收率、操作简单、可产业化的优点，且采用本发明方法所得到的产物提纯方便，提纯效率高，效果好。适用于医药中间体4‑氯‑5‑氰基嘧啶的制备厂家。

  公开号：

  CN113582933A

文献信息

• 1,2,4,5-Tetrahydro-benzo[D]azepin derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US06218385B1

  公开（公告）日：2001-04-17

  The present invention is concerned with 1,2,4,5-tetrahydro-benzo[d]azepin derivatives as well as with their pharmaceutically acceptable salts in their racemic and optically active form, which compounds are antagonists at metabotropic glutamate receptors and therefore useful for the treatment of diseases related to these receptors.

  本发明涉及1,2,4,5-四氢苯并[d]氮杂环己烷衍生物，以及它们的药用盐，无论是它们的外消旋形式还是光学活性形式，这些化合物是代谢型谷氨酸受体拮抗剂，因此对于治疗与这些受体相关的疾病是有用的。
• Compounds for treating disorders of lipid metabolism and their
  申请人：Hoechst Aktiengesellschaft

  公开号：US05773447A1

  公开（公告）日：1998-06-30

  The present invention relates to tertiary 4-amino-2-ureidopyrimidine-5-carboxamides of formula I: ##STR1## in which R.sup.1 is (C.sub.1 -C.sub.8)-alkyl wherein one or more H are replaced by F; R.sup.2 is selected from the group consisting of F, Cl, Br, H, --O--(C.sub.1 -C.sub.8)-alkyl and (C.sub.1 -C.sub.8)-alkyl, wherein one or more of the H of the alkyls can be replaced by F; R.sup.3 is selected from the group consisting of F, Cl, Br, H, --O--(C.sub.1 -C.sub.4)-alkyl and (C.sub.1 -C.sub.4)-alkyl, wherein one or more of the H of the alkyl can be replaced by F; R.sup.4 is CF.sub.3 or OCF.sub.3 ; and their physiologically tolerable salts. Process for preparing the compounds of formula I are also described. The compounds are suitable for the treatment of disorders of lipid metabolism.

  本发明涉及公式I的三级4-氨基-2-脲基嘧啶-5-羧酰胺：##STR1## 其中R.sup.1为（C.sub.1-C.sub.8）烷基，其中一个或多个H被F取代; R.sup.2选择自F，Cl，Br，H，--O--（C.sub.1-C.sub.8）烷基和（C.sub.1-C.sub.8）烷基的群，其中烷基的一个或多个H可以被F取代; R.sup.3选择自F，Cl，Br，H，--O--（C.sub.1-C.sub.4）烷基和（C.sub.1-C.sub.4）烷基的群，其中烷基的一个或多个H可以被F取代; R.sup.4为CF.sub.3或OCF.sub.3;以及其生理耐受性盐。还描述了制备公式I化合物的过程。这些化合物适用于治疗脂质代谢障碍。
• Rational design of an unusual 2D-MOF based on Cu(<scp>i</scp>) and 4-hydroxypyrimidine-5-carbonitrile as linker with conductive capabilities: a theoretical approach based on high-pressure XRD
  作者：Antonio A. García-Valdivia、Francisco J. Romero、Javier Cepeda、Diego P. Morales、Nicola Casati、Antonio J. Mota、Linda A. Zotti、Juan J. Palacios、Duane Choquesillo-Lazarte、José F. Salmerón、Almudena Rivadeneyra、Antonio Rodríguez-Diéguez

  DOI：10.1039/d0cc03564e

  日期：——

  A copper and 4-hydroxypyrimidine-5-carbonitrile based MOF presents a flexible 2D-layered structure in which, as shown by high pressure X-ray diffraction, the interlayer separation is modulated between 3.01 to 2.78 Å with varying conductive properties.

  一种基于铜和4-羟基嘧啶-5-碳腈的金属有机框架（MOF）呈现出灵活的二维层状结构，高压X射线衍射表明层间距离在3.01至2.78 Å之间调制，具有不同的导电性能。
• BROWN D. J.; IENAGA K., AUSTRAL. J. CHEM. <AJCH-AS>, 1975, 28, NO 1, 119-127
  作者：BROWN D. J.、 IENAGA K.

  DOI：——

  日期：——
• Structure–Activity Relationship Studies for Enhancer of Zeste Homologue 2 (EZH2) and Enhancer of Zeste Homologue 1 (EZH1) Inhibitors
  作者：Xiaobao Yang、Fengling Li、Kyle D. Konze、Jamel Meslamani、Anqi Ma、Peter J. Brown、Ming-Ming Zhou、Cheryl H. Arrowsmith、H. Ümit Kaniskan、Masoud Vedadi、Jian Jin

  DOI：10.1021/acs.jmedchem.6b00855

  日期：2016.8.25

  EZH2 or EZH1 (enhancer of zeste homologue 2 or 1) is the catalytic subunit of polycomb repressive complex 2 (PRC2) that catalyzes methylation of histone H3 lysine 27 (H3K27). PRC2 hyperactivity and/or hypertrimethylation of H3K27 are associated with numerous human cancers, therefore inhibition of PRC2 complex has emerged as a promising therapeutic approach. Recent studies have shown that EZH2 and EZH1

  EZH2或EZH1（zeste同源物2或1的增强剂）是多梳抑制复合物2（PRC2）的催化亚基，可催化组蛋白H3赖氨酸27（H3K27）的甲基化。PRC2的过度活跃和/或H3K27的过度三甲基化与许多人类癌症相关，因此抑制PRC2的复合体已成为一种有前途的治疗方法。最近的研究表明，EZH2和EZH1在功能上不是多余的，抑制EZH2和EZH1两者对于阻止某些癌症（如混合谱系白血病（MLL）重排的白血病）的进展是必要的。尽管EZH2抑制剂的发现取得了重大进展，但尚未进行系统的结构-活性关系（SAR）研究来研究EZH2和EZH1抑制剂之间的选择性。这里，5）研究结构变化对EZH2和EZH1抑制和选择性的影响。