4-羟基-5-嘧啶甲酸乙酯 | 4786-52-1

• 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-嘧啶甲酸乙酯
• 中文别名: 4-羟基嘧啶-5-羧酸乙酯；4-羟基嘧啶-5-甲酸乙酯；4-羟基嘧啶-5-甲酸乙脂
• 英文名称: ethyl 3,4-dihydro-4-oxopyrimidine-5-carboxylate
• 英文别名: ethyl pyrimidin-6(1H)-one-5-carboxylate；6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester；6-Oxo-1,6-dihydro-pyrimidin-5-carbonsaeure-aethylester；ethyl 6-oxo-1,6-dihydropyrimidine-5-carboxyIate；ethyl 4-oxo-3H-pyrimidine-5-carboxylate；Ethyl 4-hydroxypyrimidine-5-carboxylate；ethyl 6-oxo-1H-pyrimidine-5-carboxylate
• CAS: 4786-52-1
• 化学式: C₇H₈N₂O₃
• mdl: MFCD00194922
• 分子量: 168.152
• InChiKey: PLMIZYMXBHSARX-UHFFFAOYSA-N

物化性质

• 熔点：
  185-186 °C
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933599090
• 危险类别：
  IRRITANT
• 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: 6-Oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester
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: 6-Oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester
CAS number: 4786-52-1

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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: C7H8N2O3
Molecular weight: 168.2

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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

制备方法与用途

合成方法

4-羟基-5-嘧啶甲酸乙酯的制备方法如下：

将1.6克（70毫摩尔）金属钠加入到50毫升无水乙醇中，待反应完全后，在冰水浴中冷却至0℃。随后缓慢滴加7.3克（70毫摩尔）醋酸甲脒，并在0℃下继续反应3小时。

将1.6克（70毫摩尔）金属钠溶解于50毫升无水乙醇中，冷却到0℃后，滴加至上述反应液中。室温条件下反应过夜后，除去绝大部分的乙醇，得到黄色固体。

将该固体加入100毫升水中加热溶解，待冷却后加入100毫升乙醚，充分搅拌。分离出乙醚相并除去未完全反应的原料。再次加热至溶解，并用浓盐酸调节溶液pH值至2～3，冷却后析出淡黄色固体。过滤并进行真空干燥处理，最终得到9.4克淡黄色固体，收率为80％。

反应信息

• 作为反应物：
  描述：

  4-羟基-5-嘧啶甲酸乙酯 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以87.1%的产率得到4-氯嘧啶-5-甲酸乙酯
  参考文献：
  名称：

  杂芳化合物及其在药物中的应用

  摘要：

  本发明提供一类杂芳化合物或其立体异构体，几何异构体，互变异构体，消旋体，氮氧化物，水合物，溶剂化物，代谢产物，代谢前体以及药学上可接受的盐或前药，用于治疗增殖性疾病。本发明还公开了含有这样的化合物的药物组合物和本发明化合物或其药物组合物在制备用于治疗增殖性疾病的药物中的用途。

  公开号：

  CN104744446B
• 作为产物：
  描述：

  乙氧基甲叉丙二酸二乙酯 在 硫酸 、 双氧水 、 sodium ethanolate 作用下， 生成 4-羟基-5-嘧啶甲酸乙酯
  参考文献：
  名称：

  Synthesis of Derivatives of Pyrimidine-5-carboxylic Acid¹

  摘要：

  DOI：

  10.1021/ja01256a016

文献信息

• Aromatic heterocyclic derivatives as enzyme inhibitors
  申请人：Corvas International, Inc.

  公开号：US06342504B1

  公开（公告）日：2002-01-29

  The present invention discloses peptide aldehydes which are potent and specific inhibitors of thrombin, their pharmaceutically acceptable salts, pharmaceutically acceptable compositions thereof, and methods of using them as therapeutic agents for disease states in mammals characterized by abnormal thrombosis.

  本发明公开了肽醛，它们是凝血酶的强效和特异性抑制剂，其药用可接受的盐，药用可接受的组合物以及使用它们作为治疗哺乳动物病态血栓形成的方法。
• SUBSTITUTED PYRIMIDIN-5-CARBOXAMIDES 281
  申请人：GILL Adrian Liam

  公开号：US20090264401A1

  公开（公告）日：2009-10-22

  A compound of formula (I): and pharmaceutically-acceptable salts thereof wherein the variable groups are defined within; their use in the inhibition of 11βHSD1, processes for making them and pharmaceutical compositions comprising them are also described.

  一种具有化学式（I）的化合物： 及其药用盐，其中变量基团在其中定义；还描述了它们在抑制11βHSD1中的应用，制备它们的方法以及包含它们的药物组合物。
• 杂芳化合物及其在药物中的应用
  申请人：广东东阳光药业有限公司

  公开号：CN104744446B

  公开（公告）日：2019-06-25

  本发明提供一类杂芳化合物或其立体异构体，几何异构体，互变异构体，消旋体，氮氧化物，水合物，溶剂化物，代谢产物，代谢前体以及药学上可接受的盐或前药，用于治疗增殖性疾病。本发明还公开了含有这样的化合物的药物组合物和本发明化合物或其药物组合物在制备用于治疗增殖性疾病的药物中的用途。
• Aromatic hetherocyclic derivatives as enzyme inhibitors
  申请人：Corvas International, Inc.

  公开号：US06008351A1

  公开（公告）日：1999-12-28

  The present invention discloses peptide aldehydes which are potent and specific inhibitors of thrombin, their pharmaceutically acceptable salts, pharmaceutically acceptable compositions thereof, and methods of using them as therapeutic agents for disease states in mammals characterized by abnormal thrombosis.

  本发明公开了肽醛，它们是强效且特异的凝血酶抑制剂，其药用盐、药用组合物以及将它们用作治疗哺乳动物中由异常血栓形成特征的疾病状态的方法。
• Cyclic compounds and their use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05500427A1

  公开（公告）日：1996-03-19

  The present invention relates to a compounds represented by the following formula or salts thereof. ##STR1## The above compounds have strong angiotensin II antagonistic action, antihypertensive action and action on central nervous system, which are useful for the treatment of circulatory diseases such as hypertension, heart diseases, cerebral apoplexy, nephritis, atherosclerosis or Alzheimer's disease and senile dementia, and for agents of improving cerebral function.

  本发明涉及以下化合物或其盐所代表的化合物。上述化合物具有强大的抗肾素Ⅱ作用、降压作用和对中枢神经系统的作用，对于治疗高血压、心脏病、脑卒中、肾炎、动脉粥样硬化或阿尔茨海默病和老年性痴呆等循环系统疾病以及改善脑功能的药物非常有用。