1,3-dimethyl-5-bromo-6-methylaminopyrimidine-2,4-dione | 98333-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,3-dimethyl-5-bromo-6-methylaminopyrimidine-2,4-dione
• 英文别名: 5-bromo-1,3-dimethyl-6-methylamino-1H-pyrimidine-2,4-dione；5-Brom-1,3-dimethyl-6-methylamino-1H-pyrimidin-2,4-dion；5-Bromo-1,3-dimethyl-6-(methylamino)pyrimidine-2,4-dione
• CAS: 98333-72-3
• 化学式: C₇H₁₀BrN₃O₂
• 分子量: 248.079
• InChiKey: DUIQTNXBEVAQGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-5-bromo-6-methylaminopyrimidine-2,4-dione 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以47%的产率得到茶碱
  参考文献：
  名称：

  A High Chemical Reactivity of 5-Azidouracils and Its Synthetic Application: Novel Synthesis of 8-Substituted 1,3-Dimethylxanthine Derivatives

  摘要：

  A novel method for the preparation of 8-substituted 1,3-dimethylxanthine derivatives (7 or 8) is described: treatment of 6-alkylamino-5-bromo-1,3-dimethyluracils (6a-e), easily prepared by bromination of the corresponding 6-alkylamino-1, 3-dimethyluracils (5), with sodium azide in DMF at ambient temperature allowed the direct formation of the 8-substituted 1,3-dimethylxanthines (7) proceeding via a transient formation of the corresponding 5-azido-1 ,3-dimethyluracils. The 5-bromo-1,3-dimethyluracils (6f, g) possessing an ct-branched alkylamino group at the 6-position similarly react with sodium azide to afford 8,8-disubstituted 1,3-dimethyl-8H-xanthines (8,8-disubstituted 1,3-dimethyl-3,g-dihydropurine-2,6-diones)(8).

  DOI：

  10.3987/com-97-s68
• 作为产物：
  描述：

  6-甲氨基-1,3-二甲基脲嘧啶 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以91.2%的产率得到1,3-dimethyl-5-bromo-6-methylaminopyrimidine-2,4-dione
  参考文献：
  名称：

  一种天然产物四甲基尿酸的全合成方法

  摘要：

  本发明涉及一种天然产物四甲基尿酸的全合成方法，包括：①以1，3‑二甲基巴比妥酸为原料合成得到中间体6‑取代‑1，3‑二甲基嘧啶‑2，4‑二酮；②合成中间体1，3‑二甲基‑6‑甲氨基嘧啶‑2，4‑二酮；③合成中间体1，3‑二甲基‑5‑取代‑6‑甲氨基嘧啶‑2，4‑二酮；④合成中间体1，3‑二甲基‑5，6‑二甲氨基嘧啶‑2，4‑二酮；⑤合成中目标化合物1，3，7，9‑四甲基尿酸。该方法合成方便，且产率较高，能够在一定程度上缓解对四甲基产品的需求。

  公开号：

  CN103755705B

文献信息

• Reactions of 8,9-dihydroxanthines with acetylenic compounds. Formation of heteropropellanes.
  作者：MIKIO HORI、TADASHI KATAOKA、HIROSHI SHIMIZU、EIJI IMAI、YUKIHARU MATSUMOTO

  DOI：10.1248/cpb.33.3681

  日期：——

  Reactions of 7-substituted 1, 3, 9-trimethyl-8, 9-dihydroxanthines (3) with dimethyl acetylenedicarboxylate afforded heteropropellanes (5) in good yields. The reactions with methyl propiolate afforded pyrimidodiazepines (7) as well as propellanes (6) when the xanthines have small substituents at the 7 position. The mechanisms of formation of the products are also discussed.

  7-取代的1,3,9-三甲基-8,9-二氢黄嘌呤（3）与二甲基乙炔二羧酸酯反应，以良好的产率得到了杂螺环烷（5）。这些反应中使用丙炔酸甲酯时，当黄嘌呤在7位上有较小取代基时，既得到了嘧啶二氮杂萘（7），也生成了螺环烷（6）。同时，对产物形成的机理也进行了讨论。
• A new synthetic approach to 8-chloroflavins and their conversion into 8-(substituted-amino)flavins.
  作者：FUMIO YONEDA、KAZUO SHINOZUKA、KEIKO HIROMATSU、RYOKO MATSUSHITA、YOSHIHARU SAKUMA、MASATOMO HAMANA

  DOI：10.1248/cpb.28.3576

  日期：——

  Treatment of 5-nitro-6-(N-substituted-anilino) uracils (I) with the Vilsmeier reagent (dimethylformamide-phosphorus oxychloride) gave the corresponding 8-chloroisoalloxazines (8-chloroflavins) (II) in a single step. The conversion of I into II probably proceeds via the intermediate formation of the corresponding isoalloxazine 5-oxides (flavin 5-oxides). In fact, treatment of flavin 5-oxides with the Vilsmeier reagent also gave the 8-chloroflavins. Under the same conditions, 7-bromoflavin 5-oxides did not give the corresponding 7-bromo-8-chloroflavins, but the deoxygenated 7-bromoflavins were obtained. In this case, the Vilsmeier reagent acted as a reducing agent as well as a dehydrating and chlorinating agent. The 8-chloroflavins were converted into 8-(substituted-amino) flavins by treatment with appropriate amines.

  将5-硝基-6-(N-取代芳基氨基)尿嘧啶（I）与维尔斯梅尔试剂（N,N-二甲基甲酰胺-磷酸氧氯）反应，可以一步得到相应的8-氯异黄素（8-氯黄素）（II）。I转化为II可能经过相应的异黄素5-氧化物（黄素5-氧化物）的中间体形成。事实上，将黄素5-氧化物与维尔斯梅尔试剂反应也能得到8-氯黄素。在相同条件下，7-溴黄素5-氧化物未能得到相应的7-溴-8-氯黄素，而是获得了去氧化的7-溴黄素。在这种情况下，维尔斯梅尔试剂既充当了还原剂，又起到了脱水和氯化剂的作用。8-氯黄素通过与适当的胺反应转化为8-(取代氨基)黄素。
• Bredereck et al., Chemische Berichte, 1959, vol. 92, p. 583,594
  作者：Bredereck et al.

  DOI：——

  日期：——
• HORI, MIKIO;KATAOKA, TADASHI;SHIMIZU, HIROSHI;IMAI, EIJI;MATSUMOTO, YUKIH+, CHEM. AND PHARM. BULL., 1985, 33, N 9, 3681-3688
  作者：HORI, MIKIO、KATAOKA, TADASHI、SHIMIZU, HIROSHI、IMAI, EIJI、MATSUMOTO, YUKIH+

  DOI：——

  日期：——
• A High Chemical Reactivity of 5-Azidouracils and Its Synthetic Application: Novel Synthesis of 8-Substituted 1,3-Dimethylxanthine Derivatives
  作者：Kosaku Hirota、Magoichi Sako、Hironao Sajiki

  DOI：10.3987/com-97-s68

  日期：——

  A novel method for the preparation of 8-substituted 1,3-dimethylxanthine derivatives (7 or 8) is described: treatment of 6-alkylamino-5-bromo-1,3-dimethyluracils (6a-e), easily prepared by bromination of the corresponding 6-alkylamino-1, 3-dimethyluracils (5), with sodium azide in DMF at ambient temperature allowed the direct formation of the 8-substituted 1,3-dimethylxanthines (7) proceeding via a transient formation of the corresponding 5-azido-1 ,3-dimethyluracils. The 5-bromo-1,3-dimethyluracils (6f, g) possessing an ct-branched alkylamino group at the 6-position similarly react with sodium azide to afford 8,8-disubstituted 1,3-dimethyl-8H-xanthines (8,8-disubstituted 1,3-dimethyl-3,g-dihydropurine-2,6-diones)(8).