2-甲基-4-氨基嘧啶-5-腈 | 698-29-3

• 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-4-氨基嘧啶-5-腈
• 中文别名: 4-氨基-5-氰基-2-甲基嘧啶；4-氨基-2-甲基-5-腈；4-氨基-2甲基嘧啶-5-甲腈
• 英文名称: 2-methyl-4-amino-5-cyanopyrimidine
• 英文别名: 4-amino-2-methylpyrimidine-5-carbonitrile；4-Amino-5-cyan-2-methyl-pyrimidin；2-Methyl-4-amino-5-cyan-pyrimidin；4-amino-2-methyl-5-pyrimidine carbonitrile
• CAS: 698-29-3
• 化学式: C₆H₆N₄
• mdl: MFCD00084875
• 分子量: 134.14
• InChiKey: YBPNIILOUYAGIF-UHFFFAOYSA-N

物化性质

• 熔点：
  249 °C
• 沸点：
  315.6±27.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO、乙醇、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  6.1
• 危险品标志：
  Xn
• 安全说明：
  S36/37
• 危险类别码：
  R22,R20/21/22,R41,R37/38
• 海关编码：
  2933599090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335
• 储存条件：
  -20°C冷冻库

SDS

Name:	4-Amino-2-methylpyrimidine-5-carbonitrile 97% Material Safety Data Sheet
Synonym:
CAS:	698-29-3

Section 1 - Chemical Product MSDS Name:4-Amino-2-methylpyrimidine-5-carbonitrile 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
698-29-3	4-Amino-2-methylpyrimidine-5-carbonitr	97%	211-814-2

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. May cause respiratory tract irritation.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with 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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical 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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 698-29-3: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 249 - 252 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H6N4
Molecular Weight: 134

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 698-29-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Amino-2-methylpyrimidine-5-carbonitrile - 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
Shipping Name: NITRILES, SOLID, TOXIC, N.O.S.*
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
IMO
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
RID/ADR
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 698-29-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 698-29-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 698-29-3 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

制备方法与用途

简介

2-甲基-4-氨基嘧啶-5-腈的中文别名是4-氨基-5-氰基-2-甲基嘧啶。这是一种灰白色至黄色结晶固体，用作有机中间体。有文献报道该化合物可用于制备甾体类抗雄激素化合物，并经药理实验证明其具有良好的抗前列腺癌活性。

制备

将5kg水和5kg乙醇加入干净的20L反应瓶中，搅拌均匀后，分批加入固体氢氧化钠1.8kg并搅拌30分钟直至完全溶解。随后在冰浴下冷却至低于25℃，然后缓慢加入盐酸乙脒3.2kg，基本无放热现象，溶液呈白色浑浊状。接着，在室温条件下继续搅拌10分钟后，滴加二氰基乙酸酯的乙醇溶液。初期滴加时会释放热量，需保温在30℃以下；后期基本无放热，可加快滴加速度。完成滴加后，将反应液升温至65-70℃并保持恒温反应1.5小时。

随后，趁热将反应液缓慢倒入10kg冰水中搅拌20分钟后进行离心处理，得到湿品4.6kg。经过70-75℃鼓风干燥直至恒重后，最终获得类白色固体3.6kg，纯度为98.2%，收率为85.7%。

反应信息

• 作为反应物：
  描述：

  2-甲基-4-氨基嘧啶-5-腈 在 甲酸 作用下， 反应 4.0h， 生成 4-氨基-2-甲基嘧啶-5-甲醛
  参考文献：
  名称：

  N-酰基hydr嘧啶衍生物作为大肠杆菌PDHc E1抑制剂的设计和优化：结构-活性关系分析，生物学评估和分子对接研究

  摘要：

  通过靶向硫胺二磷酸（THDP）结合位点的大肠杆菌（大肠杆菌）丙酮酸脱氢酶多酶复合物E1（PDHC E1），一系列的THDP小说“开链”类的类似物甲，乙，和Ç与ñ -设计并合成了酰基to部分，以探讨它们在体外对大肠杆菌PHDc E1的活性，并在体内进一步评价其对微生物疾病的抑制作用。结果，A1 – 23对大肠杆菌PDHc E1表现出了中度到强效的抑制活性（IC 50 = 0.15–23.55μM）。有效的抑制剂A13，A14，A15，C2具有很强的抑制活性，对大肠杆菌PDHc E1的IC 50值为0.60、0.15、0.39和0.34μM，并且在微生物和哺乳动物之间具有良好的酶选择性抑制作用。特别是，最有效的抑制剂A14可以控制99.37％的米地黄单胞菌（Xanthimonas oryzae pv）。Oryzae。此外，化合物A14在大肠杆菌中的结合特征对PDHc E1进行了研究，以通过分子

  DOI：

  10.1016/j.bmc.2017.08.038
• 作为产物：
  描述：

  4,6-二羟基-2-甲基嘧啶 在 甲醇 、 potassium cyanate 、 Lindlar's catalyst 、 氨 、 三氯氧磷 作用下， 生成 2-甲基-4-氨基嘧啶-5-腈
  参考文献：
  名称：

  Budesinsky; Kopecky, Collection of Czechoslovak Chemical Communications, 1955, vol. 20, p. 52,56

  摘要：

  DOI：

文献信息

• [EN] cGAS ANTAGONIST COMPOUNDS<br/>[FR] COMPOSÉS ANTAGONISTES DU CGAS
  申请人：IMMUNE SENSOR LLC

  公开号：WO2017176812A1

  公开（公告）日：2017-10-12

  Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.

  揭示了一种新型化合物的化学式（I），这些化合物是cGAS拮抗剂，涉及到这些化合物的制备方法、包含这些化合物的药物组合物，以及它们在医学治疗中的应用。
• CYCLIC AMINOMETHYL PYRIMIDINE DERIVATIVE
  申请人：SUMITOMO DAINIPPON PHARMA CO., LTD.

  公开号：US20160122319A1

  公开（公告）日：2016-05-05

  The present invention provides a cyclic aminomethyl pyrimidine derivative and a pharmaceutically acceptable salt thereof with high selectivity for dopamine D 4 receptors, which are useful for treating a disease such as attention deficit hyperactivity disorder. Specifically, a compound of formula (1) or a pharmaceutically acceptable salt thereof is provided, wherein n and m are independently 1 or 2; R a is C 1-6 alkyl group, C 3-6 cycloalkyl group, or amino group; R b is hydrogen atom, C 1-6 alkyl group or the like, provided that when R a is amino group, then R b is hydrogen atom; R c1 and R c2 are independently hydrogen atom, or C 1-6 alkyl group; R d1 and R d2 are independently hydrogen atom, fluorine atom or the like; ring Q is an optionally-substituted pyridyl group or an optionally-substituted isoquinolyl group; and the bond having a dashed line is a single or double bond.

  本发明提供了一种对多巴胺D4受体具有高选择性的环状氨基甲基嘧啶衍生物及其药用盐，可用于治疗注意力缺陷多动症等疾病。具体提供了一种公式(1)的化合物或其药用盐，其中n和m独立为1或2；Ra为C1-6烷基、C3-6环烷基或氨基；Rb为氢原子、C1-6烷基等，条件是当Ra为氨基时，Rb为氢原子；Rc1和Rc2独立为氢原子或C1-6烷基；Rd1和Rd2独立为氢原子、氟原子等；环Q为可选取代的吡啶基或可选取代的异喹啉基；且虚线表示的键为单键或双键。
• 環状アミノメチルピリミジン誘導体からなる医薬
  申请人：大日本住友製薬株式会社

  公开号：JP2016108326A

  公开（公告）日：2016-06-20

  【課題】ドパミンＤ４受容体に対して選択性の高い作用を示し、注意欠陥多動性障害等の中枢神経系疾患の治療剤として有用な環状アミノメチルピリミジン誘導体及びその薬学上許容される塩の提供。【解決手段】式（１）で表される化合物またはその薬学上許容される塩。［ｎ及びｍは各々独立に１又は２；ＲａはＣ１−６アルキル基、Ｃ３−６シクロアルキル基又はアミノ基；ＲｂはＨ、Ｃ１−６アルキル基又はアルキル基で置換／未置換のアミノ基；Ｒａがアミノ基の時、ＲｂはＨ；Ｒｃ１及びＲｃ２は夫々独立にＨ、又、Ｃ１−６アルキル基；Ｒｄ１及びＲｄ２は各々独立にＨ、Ｆ又はＣ１−６のアルキル基；環Ｑは置換／未置換の５員〜１０員の含窒素ヘテロアリール基；破線を含む結合は単結合又は二重結合]【選択図】なし

  【课题】提供对多巴胺D4受体具有高选择性的作用，作为治疗注意力缺陷多动障碍等中枢神经系统疾病的药物有用的环状氨基甲基吡啶衍生物及其药物上允许的盐。 【解决手段】式（1）表示的化合物或其药物上允许的盐。[n和m各自独立为1或2；Ra为C1-6烷基、C3-6环烷基或氨基；Rb为H、C1-6烷基或烷基上取代/未取代的氨基；当Ra为氨基时，Rb为H；Rc1和Rc2分别为独立为H或C1-6烷基；Rd1和Rd2分别为独立为H、F或C1-6的烷基；环Q为取代/未取代的5至10员的含氮杂芳基；含虚线的键为单键或双键] 【选择图】无
• PYRIDO PYRIMIDINES
  申请人：Anderson Kevin

  公开号：US20120184542A1

  公开（公告）日：2012-07-19

  Compounds of formula and pharmaceutically acceptable salts thereof are described, as well as the pharmaceutical compositions containing said compounds and their pharmaceutically acceptable salts, and the use of said compounds and pharmaceutical compositions for the treatment, control or amelioration of proliferative diseases, including cancer, Down syndrome or early onset Alzheimer's disease.

  具有该公式的化合物以及它们的药用可接受盐被描述，以及包含所述化合物及其药用可接受盐的药物组合物，以及所述化合物和药物组合物用于治疗、控制或改善增生性疾病，包括癌症、唐氏综合症或早发性阿尔茨海默病的使用。
• [EN] NEW COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS RELATING THERETO<br/>[FR] NOUVEAUX COMPOSÉS, COMPOSITION PHARMACEUTIQUE ET PROCÉDÉS CORRESPONDANTS
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2010149684A1

  公开（公告）日：2010-12-29

  New compounds are disclosed which have utility in the treatment of a variety of metabolic related conditions in a patient. The compounds of this invention have the structure (I): wherein R1, R2, R3, n, p, q, and Ar are as defined herein, including stereoisomers, solvates and pharmaceutically acceptable salts thereof. Also disclosed are pharmaceutical compositions comprising a compound of this invention, as well as methods relating to the use thereof in a patient in need thereof.

  本发明公开了具有结构(I)的新化合物，其在患者中治疗各种与代谢相关的病症具有实用性：其中R1、R2、R3、n、p、q和Ar如本文所定义，包括立体异构体、溶剂合物和药学上可接受的盐。还公开了包含本发明化合物的药物组合物，以及关于其在有需要的患者中使用的方法。

表征谱图