2,4-二叔丁氧基嘧啶-5-硼酸 | 109299-79-8

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,4-二叔丁氧基嘧啶-5-硼酸
• 中文别名: 2,6-二叔丁氧基嘧啶-5-硼酸；2,4-二叔丁氧基嘧啶-5-基硼酸
• 英文名称: (2,4-di-tert-butoxypyrimidin-5-yl)boronic acid
• 英文别名: 2,4-di-t-butoxy-5-pyrimidineboronic acid；[2,4-bis[(2-methylpropan-2-yl)oxy]pyrimidin-5-yl]boronic acid
• CAS: 109299-79-8
• 化学式: C₁₂H₂₁BN₂O₄
• 分子量: 268.121
• InChiKey: SOJAZSRAXNFWRH-UHFFFAOYSA-N

物化性质

• 沸点：
  431.4±55.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  84.7
• 氢给体数：
  2
• 氢受体数：
  6

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
• 储存条件：
  -20°C下密封，并充入惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,4-Ditert-butoxypyrimidine-5-boronic acid
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: 2,4-Ditert-butoxypyrimidine-5-boronic acid
CAS number: 109299-79-8

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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, refrigerated.
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: C12H21BN2O4
Molecular weight: 268.1

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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：

  2,4-二叔丁氧基嘧啶-5-硼酸 在 四(三苯基膦)钯 、 正丁基锂 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 4.0h， 生成 2,4-Di-tert-butoxy-5-thiophen-2-yl-pyrimidine
  参考文献：
  名称：

  各种5-（溴代芳基）取代的尿嘧啶的合成

  摘要：

  我们先前进一步开发的Suzuki Pd（0）催化的弱碱性介质中的芳基硼酸与芳基溴化物或碘化物之间的偶联已用于区域选择性制备5-（2'-溴-5'-呋喃基）-， 5-（2'-溴-4'-呋喃基）-，5-（2'-溴-5'-噻吩基）-，5-（2'-溴-4'-噻吩基）-，5-（4' -溴-2'-噻唑基），5-（3'-溴苯基）-，5-（6'-溴-2'-吡啶基）-和5-（4'-溴-2'-嘧啶基）-取代2,4-二-吨-butoxypyrimidines。在这两者之间2,4-二-耦合吨丁氧基-5-嘧啶硼酸和被尝试作为偶联的九个不同的芳基二溴化物，只有2,4-和2,5- dibromothiazoles没有给出令人满意的产率，15 ％和0％。其他七个芳基二溴化物可提供所需的5-（溴芳基）-2,4-二-t-丁氧基嘧啶的产率为58-89％。尝试来合成2,4-二-吨-丁氧基-5-（2'-溴-4'-噻吩基）嘧啶从2-溴

  DOI：

  10.1002/jhet.5570320410
• 作为产物：
  描述：

  2,4-二叔丁氧基-5-溴嘧啶 在 正丁基锂 、 硼酸三乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 2,4-二叔丁氧基嘧啶-5-硼酸
  参考文献：
  名称：

  铃木-Miyaura偶联合成嘧啶的5-氟乙烯基衍生物及其与硝酮的1,3-偶极环加成反应

  摘要：

  描述了一种新型的嘧啶氟化异恶唑烷基衍生物的简单两步合成方法。该反应通过Suzuki-Miyaura偶联进行，然后与亚硝基进行高度区域选择性的1,3-偶极环加成反应。嘧啶保护基的去除导致假尿苷的氟化异恶唑烷类似物。

  DOI：

  10.1016/j.jfluchem.2011.11.005

文献信息

• Pyrimidine intermediates
  申请人：Medivir AB

  公开号：US05440040A1

  公开（公告）日：1995-08-08

  The present invention is directed to compounds of formula (I), ##STR1## wherein R.sup.1 is OH, NH.sub.2 ; R.sup.2 is a heteroaromatic or aromatic substituent; R.sup.3 is H, OH, F, OCH.sub.3 ; R.sup.4 is H, F, OH or an ether or ester residue thereof, OCH.sub.3, CN, C.dbd.CH, N.sub.3 ; R.sup.5 is OH or an ether or ester residue thereof including mono, di- and triphosphate esters (.alpha.), wherein n is 0 or 1 and M is hydrogen or a pharmaceutically acceptable counterion such as sodium, potassium, ammonium or alkylammonium; and pharmaceutically acceptable salts thereof; and pharmaceutical compositions comprising said compounds can be used for therapeutic treatment of virus infections. The present invention is also directed to compounds of formula (I'), ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, as intermediates.

  本发明涉及公式(I)的化合物：##STR1## 其中R.sup.1是OH，NH.sub.2；R.sup.2是杂芳基或芳基取代基；R.sup.3是H，OH，F，OCH.sub.3；R.sup.4是H，F，OH或其醚或酯残基，OCH.sub.3，CN，C.dbd.CH，N.sub.3；R.sup.5是OH或其醚或酯残基，包括单、二和三磷酸酯（.alpha.），其中n是0或1，M是氢或药用可接受的反离子，如钠、钾、铵或烷基铵；以及药用可接受的盐；包含这些化合物的药物组合物可用于治疗病毒感染。本发明还涉及公式(I')的化合物：##STR2## 其中R.sup.1和R.sup.2如上定义，作为中间体。
• [EN] AZETIDINECARBOXAMIDE DERIVATIVES AND THEIR USE IN THE TREATMENT OF CB1 RECEPTOR MEDIATED DISORDERS<br/>[FR] DERIVES D'AZETIDINECARBOXAMIDE ET LEUR UTILISATION DANS LE TRAITEMENT DE TROUBLES MEDIES PAR LES RECEPTEUR CB1
  申请人：VERNALIS RES LTD

  公开号：WO2004096763A1

  公开（公告）日：2004-11-11

  Compounds of formula (I) and their use in therapy, particularly for the treatment of a disorder mediated by CB1 receptors such as obesity: Formuila (I) wherein: R1 and R2 are independently selected from aryl; and R3 is hydrogen or alkyl; or a pharmaceutically acceptable salt or prodrug thereof, wherein at least one of R1 and R2 has a non-hydrogen substituent in the ortho-position(s) thereof relative to the point of attachment to the [-CH-0-] group.

  式(I)化合物及其在治疗中的应用，特别用于治疗由CB1受体介导的疾病，如肥胖症：式(I)中：R1和R2各自独立地选自芳基；R3为氢或烷基；或其药学上可接受的盐或前药，其中R1和R2中至少一个在相对于与[-CH-0-]基团连接点的邻位上具有非氢取代基。
• [EN] ARYL AND ARYLALKYL SUBSTITUTED PYRAZOLYL AND PYRIMIDINYL TRICYCLIC ENONES AS ANTIOXIDANT INFLAMMATION MODULATORS<br/>[FR] PYRAZOLYLE SUBSTITUÉ PAR UN ARYLE ET ARYLALKYLE ET PYRIMIDINYL ÉNONES TRICYCLIQUES COMME MODULATEURS ANTIOXYDANTS DE L'INFLAMMATION
  申请人：ABBVIE INC

  公开号：WO2015112792A1

  公开（公告）日：2015-07-30

  The present application relates to: (a) compounds of Formula (I): and salts thereof, wherein R1, R2, R3, R4, R5, R6, m, n, X and Y are as defined in the specification; (b) compositions comprising such compounds and salts; and (c) methods of use of such compounds, salts, and compositions, particularly use for the treatment and prevention of diseases such as those associated with oxidative stress and inflammation.

  本申请涉及：(a) 公式(I)的化合物及其盐，其中R1、R2、R3、R4、R5、R6、m、n、X和Y如规范中所定义；(b) 包含这些化合物和盐的组合物；以及(c) 使用这些化合物、盐和组合物的方法，特别是用于治疗和预防与氧化应激和炎症相关的疾病。
• Synthesis of various 5-substituted uracils
  作者：Dan Peters、Anna-Britta Hörnfeldt、Salo Gronowitz

  DOI：10.1002/jhet.5570270756

  日期：1990.11

  Several Pd-catalyzed coupling reactions have been evaluated for the synthesis of 5-substituted uracils. A convenient reaction, further developed by us, is the Suzuki Pd(0)-catalyzed coupling between arylboronic acids and aryl bromides or iodides in weakly alkaline medium. However, all attempts to use 5-bromo- or 5-iodouracil as the aryl halide failed. On the other hand, couplings between 2,4-di-t-

  已评估了几种Pd催化的偶联反应，用于合成5取代的尿嘧啶。由我们进一步开发的一种方便的反应是在弱碱性介质中芳基硼酸与芳基溴化物或碘化物之间的Suzuki Pd（0）催化偶联。但是，所有使用5-溴-或5-碘尿嘧啶作为卤代芳基的尝试均告失败。在另一方面，2,4-二-之间的耦合吨丁氧基-5-溴嘧啶和各种芳基硼酸是成功的。在当芳基硼酸是不可用的情况下，这是更好扭转耦合功能，并使用2,4-二-吨-丁氧基-5-嘧啶硼酸和芳基溴化物。以此方式制备了大量的5-芳基尿嘧啶。它们是通过5-芳基-2,4-二-的脱烷基作用以几乎定量的产率获得的叔丁氧基嘧啶。然而，这些方法的最大缺点是2,4-二氯-5-溴嘧啶，其为2,4-二-的合成中的中间体的高过敏性质吨丁氧基-5-溴嘧啶和2,4-二Ť-丁氧基-5-嘧啶硼酸。为了避免这种中间体，尝试了5-溴-2，4-二三甲基甲硅烷基氧基嘧啶和芳基硼酸之间的偶联，但是失败了。此外，由
• PYRIMIDINE DERIVATIVES
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP1595869A1

  公开（公告）日：2005-11-16

  The present invention provides a pyrimidine derivative represented by Formula (I) [wherein Ar represents substituted or unsubstituted aryl, etc., R1 represents -NR2R3 (wherein R2 represents a hydrogen atom or substituted or unsubstituted lower alkyl and R3 represents substituted or unsubstituted lower alkyl, substituted or unsubstituted aralkyl, etc.), etc. A represents a single bond, Formula (III) (wherein m1 represents an integer of 0 to 2, n1 represents an integer of 0 to 4, a1 represents a number ranging from 0 to a substitutable number, R5 represents substituted or unsubstituted lower alkyl, etc. and each R5 may be the same or different when a1 is 2 or more), etc. and Q represents -NR6R7 (wherein R6 and R7 may be the same or different and each represents a hydrogen atom, a substituted or unsubstituted heteroalicyclic group, etc.), a substituted or unsubstituted heteroalicyclic group, substituted or unsubstituted piperidin-4-ylamino, etc.], or quaternary ammonium salts thereof, or pharmaceutically acceptable salts thereof which have anti-inflammatory activities, modulating activities on TARC and/or MDC functions and the like, and are useful for treating and/or preventing diseases which is related to T cells such as allergic diseases, autoimmune diseases, transplant rejection, etc.

  本发明提供了一种由式（I）表示的嘧啶衍生物[其中Ar代表取代或未取代的芳基等，R1代表-NR2R3（其中R2代表氢原子或取代或未取代的较低烷基，R3代表取代或未取代的较低烷基、取代或未取代的芳基烷基等），等。A代表单键，式（III）（其中m1代表0至2的整数，n1代表0至4的整数，a1代表从0到可取代数的数字，R5代表取代或未取代的较低烷基等，每个R5在a1为2或更多时可以相同或不同），等，Q代表-NR6R7（其中R6和R7可以相同或不同，且每个代表氢原子、取代或未取代的杂环烷基等），取代或未取代的杂环烷基，取代或未取代的哌啶-4-基氨基等]，或其季铵盐，或其药用可接受盐，具有抗炎活性、调节TARC和/或MDC功能等，适用于治疗和/或预防与T细胞相关的疾病，如过敏性疾病、自身免疫性疾病、移植排斥等。