嘧啶-2-硫代甲酰胺 | 4537-73-9

• 物质功能分类: 医药中间体 - 杂环化合物
• 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: 嘧啶-2-硫代甲酰胺
• 中文别名: 2-嘧啶硫代酰胺；嘧啶-2-硫代酰胺；2-嘧啶硫代甲酰胺
• 英文名称: pyrimidine-2-carbothioamide
• CAS: 4537-73-9
• 化学式: C₅H₅N₃S
• mdl: MFCD12093703
• 分子量: 139.181
• InChiKey: QAUHVPUYFSGVME-UHFFFAOYSA-N

物化性质

• 熔点：
  225 °C
• 沸点：
  327.3±25.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 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：
  83.9
• 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,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Name:	2-Pyrimidinethiocarboxamide Material Safety Data Sheet
Synonym:	None
CAS:	4537-73-9

Section 1 - Chemical Product MSDS Name:2-Pyrimidinethiocarboxamide Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4537-73-9	2-Pyrimidinethiocarboxamide	ca 100	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 4537-73-9: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: orange-red
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C5H5N3S
Molecular Weight: 139.1151

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, oxides of sulfur, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4537-73-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Pyrimidinethiocarboxamide - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 4537-73-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 4537-73-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4537-73-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  嘧啶-2-硫代甲酰胺 在 亚甲兰 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以25.7 mg的产率得到2-氰基嘧啶
  参考文献：
  名称：

  Metal-free dehydrosulfurization of thioamides to nitriles under visible light

  摘要：

  使用可见光介导的噻酰胺向腈的脱硫化反应已经被证明，使用有机染料作为光催化剂，空气作为氧化剂。

  DOI：

  10.1039/d0cc01380c
• 作为产物：
  描述：

  2-氰基嘧啶 在 硫化氢 作用下， 生成 嘧啶-2-硫代甲酰胺
  参考文献：
  名称：

  芳胺修饰的噻唑作为供体-受体染料：电荷转移过程的量子化学评价和作为钌 (II) 配合物中配体的测试

  摘要：

  合成了一系列带有不同芳胺组分（三芳胺、咔唑和吩噻嗪）作为电子供体和氮杂杂环组分（吡啶、吡嗪和嘧啶）作为电子受体部分的新型 4-羟基-1,3-噻唑基发色团。对两种选定的化合物进行了精细的量子化学计算，以确定 HOMO/LUMO 跃迁和分子内电荷转移状态的性质。研究了电化学性质：染料显示出可逆的第一氧化和还原峰，前者主要受芳胺类型的支配。供体部分在 Buchwald-Hartwig 条件下合成。几个提出的 X 射线结构提供了对配体几何形状的更深入的了解。发色团的双齿性质使其适合作为过渡金属络合物中的配体。相应的钌 (II) 多吡啶配合物 - Ru(dmbpy)2(L)(PF6)2 (dmbpy = 4,4'-二甲基-2,2'-联吡啶) - 成功合成了七个配体。这些复合物中的 MLCT 带显着加宽，从而提高了光捕获效率。

  DOI：

  10.1002/ejoc.201200688

文献信息

• Synthesis and Characterization of the Novel Rodent-Active and CNS-Penetrant P2X7 Receptor Antagonist Lu AF27139
  作者：Allen T. Hopper、Martin Juhl、Jorrit Hornberg、Lassina Badolo、John Paul Kilburn、Annemette Thougaard、Gennady Smagin、Dekun Song、Londye Calice、Veena Menon、Elena Dale、Hong Zhang、Manuel Cajina、Megan E. Nattini、Adarsh Gandhi、Michel Grenon、Ken Jones、Tanzilya Khayrullina、Gamini Chandrasena、Christian Thomsen、Stevin H. Zorn、Robb Brodbeck、Suresh Babu Poda、Roland Staal、Thomas Möller

  DOI：10.1021/acs.jmedchem.0c02249

  日期：2021.4.22

  insufficient number of P2X7 receptor antagonists with adequate rodent potency, CNS permeability, and pharmacokinetic properties from which to evaluate CNS disease hypotheses preclinically. Herein, we describe the molecular pharmacology, safety, pharmacokinetics, and functional CNS target engagement of Lu AF27139, a novel rodent-active and CNS-penetrant P2X7 receptor antagonist. Lu AF27139 is highly selective

  仍然缺乏足够数量的具有足够啮齿动物效力，中枢神经系统通透性和药代动力学性质的P2X7受体拮抗剂，可以从临床上评估中枢神经系统疾病假说。在这里，我们描述了Lu AF27139（一种新型的啮齿动物活性和CNS渗透性P2X7受体拮抗剂）的分子药理学，安全性，药代动力学和功能性CNS靶标结合。Lu AF27139具有高度选择性，对大鼠，小鼠和人类形式的受体具有强大的作用。大鼠的药代动力学特性良好，口服生物利用度高，清除率适中（0.79 L /（h kg）），并且具有良好的CNS渗透性。脂多糖（LPS）引发和2'（3'）- O的体内小鼠CNS微透析研究-（苯甲酰基苯甲酰基）腺苷-5'-三磷酸（BzATP）诱导的IL-1β释放证明功能性中枢神经系统靶标参与。重要的是，Lu AF27139在标准的体外和体内毒性研究中没有作用。基于这些特性，我们相信Lu AF27139将是探索P2X7受体在中枢神经系统疾病的啮齿动物模型中的重要工具。
• Studies on non-steroidal inhibitors of aromatase enzyme; 4-(aryl/heteroaryl)-2-(pyrimidin-2-yl)thiazole derivatives
  作者：Zafer Sahin、Merve Ertas、Barkın Berk、Sevde Nur Biltekin、Leyla Yurttas、Seref Demirayak

  DOI：10.1016/j.bmc.2018.02.048

  日期：2018.5

  Steroidal and non-steroidal aromatase inhibitors target the suppression of estrogen biosynthesis in the treatment of breast cancer. Researchers have increasingly focused on developing non-steroidal derivatives for their potential clinical use avoiding steroidal side-effects. Non-steroidal derivatives generally have planar aromatic structures attached to the azole ring system. One part of this ring

  甾体和非甾体芳香酶抑制剂的目标是在乳腺癌的治疗中抑制雌激素的生物合成。研究人员越来越多地致力于开发非甾体衍生物以用于其潜在的临床用途，从而避免甾体副作用。 非甾族衍生物通常具有连接至唑环系统的平面芳族结构。该环系统的一部分包含通过芳香化酶的血红素基团的配位抑制芳香化的官能团。三唑环系统的取代和侧链芳族/环状结构的发展可以增加对芳香酶抑制的选择性。 在这项研究中，合成了4-（芳基/杂芳基）-2-（嘧啶-2-基）噻唑衍生物，并进行了物理分析和结构确定研究。通过基于荧光的芳香化酶抑制测定法确定IC 50值，并且发现化合物1（4-（2-羟苯基）-2-（嘧啶-2-基）噻唑）是有效的酶抑制剂（IC 50：0.42 nM） 。然后，使用3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物（MTT）分析评估了它们对MCF-7和HEK-293细胞系的抗增殖活性。化合物1，7，8，13，15，18，2
• One-Pot Strategy for Thiazoline Synthesis from Alkenes and Thioamides
  作者：Nur-E Alom、Fan Wu、Wei Li

  DOI：10.1021/acs.orglett.7b00079

  日期：2017.2.17

  convenient synthesis of a privileged pharmaceutical motif, thiazoline is accomplished. This reaction utilizes simple and readily available alkene and thioamide substrates in an intermolecular fashion via a simple one-pot procedure. A wide range of functional groups is tolerated, and the thiazoline product has been further utilized for the synthesis of the corresponding β-aminothiol and thiazole from routine

  完成了特有药物基序噻唑啉的方便合成。该反应通过简单的一锅法以分子间方式利用简单且容易获得的烯烃和硫代酰胺底物。宽泛的官能团是可以耐受的，噻唑啉产物已被进一步用于从常规水解和氧化方案合成相应的β-氨基硫醇和噻唑。
• Arylamine-Modified Thiazoles as Donor-Acceptor Dyes: Quantum Chemical Evaluation of the Charge-Transfer Process and Testing as Ligands in Ruthenium(II) Complexes
  作者：Roberto Menzel、Stephan Kupfer、Ralf Mede、Dieter Weiß、Helmar Görls、Leticia González、Rainer Beckert

  DOI：10.1002/ejoc.201200688

  日期：2012.9

  deeper insight into the geometries of the ligands. The bidentate nature of the chromophores makes them suitable as ligands in transition metal complexes. The corresponding ruthenium(II) polypyridine complexes – Ru(dmbpy)2(L)(PF6)2 (dmbpy = 4,4′-dimethyl-2,2′-bipyridine) – were successfully synthesized for seven of the ligands. The MLCT bands in these complexes are significantly broadened, resulting in

  合成了一系列带有不同芳胺组分（三芳胺、咔唑和吩噻嗪）作为电子供体和氮杂杂环组分（吡啶、吡嗪和嘧啶）作为电子受体部分的新型 4-羟基-1,3-噻唑基发色团。对两种选定的化合物进行了精细的量子化学计算，以确定 HOMO/LUMO 跃迁和分子内电荷转移状态的性质。研究了电化学性质：染料显示出可逆的第一氧化和还原峰，前者主要受芳胺类型的支配。供体部分在 Buchwald-Hartwig 条件下合成。几个提出的 X 射线结构提供了对配体几何形状的更深入的了解。发色团的双齿性质使其适合作为过渡金属络合物中的配体。相应的钌 (II) 多吡啶配合物 - Ru(dmbpy)2(L)(PF6)2 (dmbpy = 4,4'-二甲基-2,2'-联吡啶) - 成功合成了七个配体。这些复合物中的 MLCT 带显着加宽，从而提高了光捕获效率。
• [EN] INHIBITOR OF THE P2X7 RECEPTOR<br/>[FR] INHIBITEUR DU RÉCEPTEUR P2X7
  申请人：H LUNDBECK AS

  公开号：WO2017076825A1

  公开（公告）日：2017-05-11

  The present invention provides (S)-N-(2-(4-chlorophenyl)-2-morpholinoethyl)-2- (pyrimidin-2-yl)-4-(trifluoromethyl)thiazole-5-carboxamide as P2X7 inhibitor, its use as a medicament, and a convenient enantiomeric synthesis protocol for the preparation of (S)- N-(2-(4-chlorophenyl)-2-morpholinoethyl)-2-(pyrimidin-2-yl)-4-(trifluoromethyl)thiazole-5-carboxamide.

  本发明提供了(S)-N-(2-(4-氯苯基)-2-吗啡基乙基)-2-(嘧啶-2-基)-4-(三氟甲基)噻唑-5-羧酰胺作为P2X7抑制剂，其作为药物的用途，以及一种方便的对映体合成方案，用于制备(S)-N-(2-(4-氯苯基)-2-吗啡基乙基)-2-(嘧啶-2-基)-4-(三氟甲基)噻唑-5-羧酰胺。