2-嘧啶羧酰胺 | 88511-48-2

• 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-嘧啶羧酰胺
• 中文别名: 嘧啶-2-甲酰胺
• 英文名称: pyrimidine-2-carboxamide
• 英文别名: 2-Pyrimidinecarboxamide
• CAS: 88511-48-2
• 化学式: C₅H₅N₃O
• 分子量: 123.114
• InChiKey: FUXJMHXHGDAHPD-UHFFFAOYSA-N

物化性质

• 熔点：
  166-167 °C
• 沸点：
  332.0±25.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Pyrimidinecarboxamide
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-Pyrimidinecarboxamide
CAS number: 88511-48-2

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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: C5H5N3O
Molecular weight: 123.1

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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：

  2-嘧啶羧酰胺 在 乙醚 、 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：

  2-氰基嘧啶 在 copper(l) iodide 、 caesium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 硝基甲烷 、 水 为溶剂， 反应 7.0h， 以51%的产率得到2-嘧啶羧酰胺
  参考文献：
  名称：

  Nitrile Hydration Reaction Using Copper Iodide/Cesium Carbonate/DBU in Nitromethane–Water

  摘要：

  在铜碘化物/碳酸铯/1,8-二氮杂双环[5.4.0]十一烯/硝基甲烷-水体系中描述了催化腈水合作用（酰胺形成）。该方案稳健可靠；它可应用于广泛的底物，并具有高化学选择性。

  DOI：

  10.1055/s-0037-1609912

文献信息

• Parallel Synthesis of 1<i>H-</i>Pyrazolo[3,4-<i>d</i>]pyrimidines via Condensation of <i>N</i>-Pyrazolylamides and Nitriles
  作者：Akshay A. Shah、Lois K. Chenard、Joseph W. Tucker、Christopher J. Helal

  DOI：10.1021/acscombsci.7b00116

  日期：2017.11.13

  A novel parallel medicinal chemistry (PMC)-enabled synthesis of 1H-pyrazolo[3,4-d]pyrimidines employing condensation of easily accessible N-pyrazolylamides and nitriles has been developed. The presented studies describe singleton and library enablements that allowed rapid generation of molecular diversity to examine C4 and C6 vectors. This chemistry enabled access to challenging alkyl substituents

  已开发出一种新颖的平行药物化学（PMC）合成1 H-吡唑并[3,4- d ]嘧啶的方法，该方法采用易于获得的N-吡唑烷基酰胺和腈的缩合反应。提出的研究描述了单例和库使能，其允许快速产生分子多样性来检查C4和C6载体。这种化学性质使人们能够使用具有挑战性的烷基取代基，从而扩大了整个化学空间，使其超过了典型的C（sp 2）–C（sp 2）偶联和S N Ar转化所能提供的空间。此外，讨论了允许使用更大和更多样化的酰胺和羧酸作为腈前体的单体基团互变。
• [EN] IRAK DEGRADERS AND USES THEREOF<br/>[FR] AGENTS DE DÉGRADATION D'IRAK ET LEURS UTILISATIONS
  申请人：KYMERA THERAPEUTICS INC

  公开号：WO2020264499A1

  公开（公告）日：2020-12-30

  The present invention provides compounds, compositions thereof, and methods of using the same. The compounds include an IRAK binding moiety capable of binding to IRAK4 and a degradation inducing moiety (DIM). The DIM could be DTM a ligase binding moiety (LBM) or lysine mimetic. The compounds could be useful as IRAK protein kinase inhibitors and applied to IRAK mediated disorders.

  本发明提供了化合物、其组合物以及使用这些化合物的方法。这些化合物包括能够结合到IRAK4的IRAK结合基团和诱导降解的基团（DIM）。DIM可以是DTM、一个连接酶结合基团（LBM）或赖氨酸类似物。这些化合物可以作为IRAK蛋白激酶抑制剂，并应用于IRAK介导的疾病。
• 一种腈水解合成酰胺的方法
  申请人：南京理工大学

  公开号：CN104744288B

  公开（公告）日：2017-01-04

  本发明公开了一种腈水解合成酰胺的方法。在反应容器中，加入腈，乙醛肟，水，水溶性铑络合物，反应混合物在50‑80 oC下反应数小时后，冷却到室温。加入乙酸乙酯进行萃取，得有机层，旋转蒸发除去溶剂，得到目标产物。同现有的过渡金属催化使用肟作水源腈水解合成酰胺的方法相比，本发明所使用的催化剂负载低，不含有环境污染严重的膦配体，在空气中就能进行，不需要氮气保护。因此，该反应符合绿色化学的要求，具有广阔的发展前景。
• Arene-ruthenium(II)-phosphine complexes: Green catalysts for hydration of nitriles under mild conditions
  作者：Komal M. Vyas、Poulami Mandal、Rinky Singh、Shaikh M. Mobin、Suman Mukhopadhyay

  DOI：10.1016/j.inoche.2019.107698

  日期：2020.2

  catalyst concluded a structural-activity relationship for the higher catalytic activity of [Ru]-1, being able to convert huge variety of aromatic, heteroaromatic and aliphatic nitriles. The use of eco-friendly water as a solvent, open atmosphere and avoidance of any organic solvent during the catalytic reactions prove the reported process to be truly green and sustainable.

  摘要 将[RuCl(μ-Cl)(η6-芳烃)}2](η6-芳烃=对伞花烃)二聚体与三(2-呋喃基)膦(PFu3 )和1,3,5-三氮杂-7-磷金刚烷(PTA)，分别得到[RuCl2(η6-芳烃)PFu3][Ru]-1、[RuCl(η6-芳烃)(PFu3)(PTA)]BF4 [Ru]-2 和 [RuCl(η6-芳烃)(PFu3)2]BF4 [Ru]-3。使用分析和光谱方法（包括单晶 X 射线研究）对所有复合物进行结构鉴定。探索了所得配合物作为潜在均相催化剂的有效性，用于在水性介质和空气气氛中将不同的腈选择性水合成相应的酰胺。取决于磷供体配体的性质和数量以及可用于催化的位点，催化剂的催化活性存在显着差异。使用高效催化剂的结构类似物进行的实验研究得出结论，[Ru]-1 具有较高催化活性的结构-活性关系，能够转化种类繁多的芳香族、杂芳香族和脂肪族腈。在催化反应过程中使用环保水作为溶剂、开放的气氛
• Selective transformation of nitriles into amides and carboxylic acids by an immobilized nitrilase
  作者：Norbert Klempier、Anna de Raadt、Kurt Faber、Herfried Griengl

  DOI：10.1016/s0040-4039(00)92623-6

  日期：1991.1

  Using an immobilized nitrilase from Rhodococcus sp. mild and selective hydrolysis of nitriles can be achieved even in the presence of acid or base sensitive groups under neutral conditions. This method is applicable to a broad range of substrates as exemplified by aliphatic, alicyclic, heterocyclic and carbohydrate type nitriles.

  使用来自红球菌属的固定化腈水解酶。即使在中性条件下存在酸或碱敏感基团，也可以实现腈的温和选择性水解。该方法适用于各种底物，例如脂族，脂环族，杂环和碳水化合物类腈。