5,6-二甲基呋喃[2,3-d]嘧啶-4-胺 | 5117-94-2

• 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 - 呋喃[2,3-d]嘧啶
• 中文名称: 5,6-二甲基呋喃[2,3-d]嘧啶-4-胺
• 中文别名: 5,6-二甲基呋喃并[2,3-D]嘧啶-4-胺
• 英文名称: 5,6-dimethylfuro[2,3-d]pyrimidin-4-amine
• 英文别名: 5,6-dimethyl-furo[2,3-d]pyrimidin-4-ylamine
• CAS: 5117-94-2
• 化学式: C₈H₉N₃O
• mdl: MFCD01002271
• 分子量: 163.179
• InChiKey: BCCQRVLPINNELE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5,6-二甲基呋喃[2,3-d]嘧啶-4-胺 在 二溴甲烷 、 亚硝酸异戊酯 作用下， 反应 1.0h， 以47%的产率得到4-Bromo-5,6-dimethylfuro[2,3-d]pyrimidine
  参考文献：
  名称：

  Aroylation of Fused Pyrimidines; Synthesis of 4-Aroylfuro[2,3-d]-, 4-Aroylthieno[2,3-d]-, and 4-Aroylisoxazolo[5,4-d]pyrimidines

  摘要：

  4-Aroylfuro[2,3-d]-(4), 4-aroylthieno[2,3-d]-(7 and 8), and 4-aroylisoxazolo[5,4-d]pyrimidines (13) were synthesized by aroylation of the fused chloro-(3a and 12) or bromopyrimidines (3b, 5, and 6) with arenecarbaldehydes (2) catalyzed by an imidazolium salt (1a). The fused aroylpyrimidines (4 and 7) were also synthesized by oxidative decyanation of alpha-phenylheteroareneacetonitriles (10 and 11).

  DOI：

  10.3987/com-97-7914
• 作为产物：
  描述：

  聚合甲醛 、 2-氨基-4,5-二甲基-3-呋喃甲腈 在 乙酸酐 作用下， 反应 2.0h， 以58%的产率得到5,6-二甲基呋喃[2,3-d]嘧啶-4-胺
  参考文献：
  名称：

  Preparation of Heteroarenecarbonitriles by Reaction of Haloheteroarenes with Potassium Cyanide Catalyzed by Sodium p-Toluenesulfinate

  摘要：

  Several heteroarenecarbonitriles were prepared by reaction of haloheteroarenes with potassium cyanide catalyzed by sodium p-toluenesulfinate (1) or sodium methanesulfinate (2). In the reaction pathway, the cyanation proceeds through the formation of the sulfonylheteroarenes.

  DOI：

  10.3987/com-94-s(b)38

文献信息

• [EN] SUBSTITUTED DIHYDROIMIDAZOPYRIDINEDIONES AS MKNK1 AND MKNK2 INHIBITORS<br/>[FR] DIHYDROIMIDAZOPYRIDINEDIONES SUBSTITUÉES UTILISÉES EN TANT QU'INHIBITEURS DE MKNK1 ET DE MKNK2
  申请人：BAYER PHARMA AG

  公开号：WO2018134148A1

  公开（公告）日：2018-07-26

  The present invention relates to substituted dihydroimidazopyridinedione compounds of general formula (A) as described and defined herein, to methods of preparing said compounds, to intermediate compounds useful for preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of a hyperproliferative, angiogenesis disorders, inflammatory diseases or diseases associated with inflammatory pain, as a sole agent or in combination with other active ingredients.

  本发明涉及通式（A）所描述和定义的取代二氢咪唑吡啶二酮化合物，以及制备该化合物的方法，用于制备该化合物的有用中间体化合物，包含该化合物的药物组合物和复合物，以及利用该化合物制造用于治疗或预防疾病的药物组合物，特别是治疗过度增殖、血管生成障碍、炎症性疾病或与炎症性疼痛相关的疾病的药物组合物，作为单一药剂或与其他活性成分结合使用。
• Microwave Assisted Gould-Jacob Reaction in the Synthesis of Furopyrimidopyrimidines and Their Transformation via Ring Opening to Aminoesters
  作者：Nirmal M. Shah、Vivek C. Ramani、Rina D. Shah

  DOI：10.14233/ajchem.2017.20873

  日期：——

  Gould-Jacob reaction is well-known for the construction of fused pyrimidopyrimidines from pyrimidineamines and diethyl ethoxymethylenemalonate (EMME) or acyl malonic ester. Ethyl 4-oxo-8,9-disubstitutedfuro[3,2-e]pyrimidine-3-carboxylates (3) has been carried out by classical heating from furo[2,3-d]pyrimidine-4-amines (1) and diethyl ethoxymethylenemalonate through the formation of uncyclized diethyl N-[5,6-substituted-7H-[2,3-d]pyrimidin-4-yl]aminomethylenemalonates (2) as an intermediate. The identical compound 3 have also been synthesized via rapid solvent free microwave irradiation method. A comparison of classical method versus solvent-free microwave irradiation method has been studied. The reaction of compound 3 has also been explored with alcoholic NaOH and hydrazine hydrate to synthesize corresponding acid 4 and acid hydrazide derivatives 5. Reaction of compound 3 with hydrazine hydrate failed to yield acid hydrazide, but they underwent unexpected ring opening and transformed to respective aminoester 6.

  古尔德-雅各布反应（Gould-Jacob reaction）是由嘧啶胺和乙氧基甲叉丙二酸二乙酯（EMME）或丙二酸酰酯生成融合嘧啶并嘧啶的著名反应。4-氧代-8,9-二取代呋喃并[3,2-e]嘧啶-3-羧酸乙酯（3）是以呋喃并[2,3-d]嘧啶-4-胺（1）和乙氧基甲叉丙二酸二乙酯为中间体，通过形成未环化的 N-[5,6-取代-7H-[2,3-d]嘧啶-4-基]氨甲基丙二酸二乙酯（2），经传统加热方法合成的。相同的化合物 3 也是通过快速无溶剂微波辐照法合成的。研究人员对传统方法和无溶剂微波辐照方法进行了比较。还研究了化合物 3 与醇 NaOH 和水合肼的反应，以合成相应的酸 4 和酸酰肼衍生物 5。化合物 3 与水合肼的反应未能生成酸酰肼，但它们发生了意想不到的开环反应，并转化成了相应的氨基酯 6。
• Expedient Access to 18F‐Fluoroheteroarenes via Deaminative Radiofluorination of Aniline‐Derived Pyridinium Salts
  作者：Joseph Ford、Sebastiano Ortalli、Zijun Chen、Jeroen B. I. Sap、Matthew Tredwell、Véronique Gouverneur

  DOI：10.1002/anie.202404945

  日期：2024.6.21

  18F-Fluoroheteroarenes find wide application as radiotracers for PET (positron emission tomography) imaging. Here, we present a deaminative radiosynthetic approach via pyridinium tetrafluoroborates that facilitates radiofluorination of 33 structurally diverse heteroarenes in up to 98 % RCY (radiochemical yield). This method was also amenable to automation and was successfully translated to an automated

  18 F-氟杂芳烃广泛用作 PET（正电子发射断层扫描）成像的放射性示踪剂。在这里，我们提出了一种通过四氟硼酸吡啶的脱氨基放射合成方法，可促进 33 种结构不同的杂芳烃的放射氟化，RCY（放射化学产率）高达 98%。该方法也适合自动化，并成功转化为自动合成器。
• Gewald,K., Chemische Berichte, 1966, vol. 99, p. 1002 - 1007
  作者：Gewald,K.

  DOI：——

  日期：——