6-bromo-1,3-dimethyluracil | 21428-17-1

• 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: 6-bromo-1,3-dimethyluracil
• 英文别名: 6-Brom-1,3-dimethyluracil；6-bromo-1,3-dimethyl-1H-pyrimidine-2,4-dione；6-bromo-1,3-dimethylpyrimidine-2,4-dione
• CAS: 21428-17-1
• 化学式: C₆H₇BrN₂O₂
• 分子量: 219.038
• InChiKey: XXZGZBJOMBOIJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-bromo-1,3-dimethyluracil 在 N-甲基吗啉 、 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 、 sodium nitrite 作用下， 以 甲醇 、 水 、 异丙醇 为溶剂， 20.0~120.0 ℃ 、101.33 kPa 条件下， 反应 41.5h， 生成 1,3-dimethyl-9-[(1,3-dioxolan-2-yl)methyl]-3,9-dihydro-1H-purine-2,6-dione
  参考文献：
  名称：

  一种多索茶碱杂质A的制备方法

  摘要：

  本发明涉及药物化学领域，针对多索茶碱杂质A只能采用提取的方法获得且所得产物的产量低的问题，提供了一种多索茶碱杂质A的制备方法，包括以下步骤：S1、在缚酸剂的作用下，1,3‑二甲基‑6‑卤代尿嘧啶与氨基乙醛缩二醇在溶剂中发生缩合反应，得到化合物Ⅲ；S2、在酸作用下，化合物Ⅲ与亚硝化试剂在极性溶剂中进行亚硝化反应，得到化合物Ⅳ；S3、在催化剂作用下，化合物Ⅳ在极性溶剂中经还原剂还原得到化合物Ⅴ；S4、在有机酸催化作用下，化合物Ⅴ与环化试剂成环得到化合物Ⅵ；S5、在有机酸催化作用下，化合物Ⅵ与乙二醇进行缩醛交换反应得到多索茶碱杂质A。通过采用上述方法制备，制备原料易于获得、制备工艺简单、制备周期短、产量高。

  公开号：

  CN113045572A

文献信息

• New and Efficient Palladium(0)-Mediated Microwave-Assisted Direct C3 Alkenylation of Imidazo[1,2-<i>a</i>]pyridines
  作者：Sabine Berteina-Raboin、Jamal Koubachi、Saïd El Kazzouli、Abderrahim Mouaddib、Gérald Guillaumet

  DOI：10.1055/s-2008-1067181

  日期：2008.8

  2-a]pyridines in high to moderate yields by microwave direct palladium-catalyzed C-H alkenylation between bromoalkenes and imidazo[1,2-a]pyridines. The scope and limitation of the palladium(0)-catalyzed alkenylation method were investigated. Optimized conditions were successfully applied to a wide variety of imidazo[1,2-a]pyridine derivatives and bromoalkenes. The compatibility of the synthesis with

  在本文中，我们介绍了通过微波直接钯催化溴代烯烃和咪唑并[1,2-a]吡啶之间的CH 烯基化以高至中等收率合成3-烯基咪唑并[1,2-a] 吡啶。研究了钯（0）催化的烯基化方法的范围和局限性。优化的条件已成功应用于多种咪唑并[1,2-a]吡啶衍生物和溴代烯烃。研究了在 6 位存在氯取代基时合成的相容性。使用 Suzuki 交叉偶联条件对 6-氯咪唑并[1,2-a]吡啶进行官能化，得到多官能团化合物。
• A Raman-active competitive inhibitor of OMP decarboxylase
  作者：Brian P. Callahan、Alasdair F. Bell、Peter J. Tonge、Richard Wolfenden

  DOI：10.1016/j.bioorg.2005.12.001

  日期：2006.4

  6-Cyanouridine 5'-phosphate was shown to act as a competitive inhibitor of yeast OMP decarboxylase, with a K-i value of 1.1 X 10(-5) M. Upon binding by the active site of yeast OMP decarboxylase (EC 4.1.1.23), the Raman stretching frequency of the nitrile group of 6-cyanouridine 5'-phosphate decreases from 2240 to 2225 cm(-1). Based on the behavior of a model compound, 6-cyano-1,3-dimethyluracil, and on vibrational calculations, the observed change in stretching frequency is attributed to desolvation of the ligand, and distortion of the ligand in which the nitrile group moves out of the plane of the pyrimidine ring. Similar distortions may play a role in substrate activation by OMP decarboxylase, contributing to the catalytic process. (c) 2005 Elsevier Inc. All rights reserved.
• Farkas, Lajos; Keuler, Josef; Wamhoff, Heinrich, Chemische Berichte, 1980, vol. 113, # 7, p. 2566 - 2574
  作者：Farkas, Lajos、Keuler, Josef、Wamhoff, Heinrich

  DOI：——

  日期：——
• A Formal [3 + 3] Cycloaddition Reaction. 5. An Enantioselective Intramolecular Formal Aza-[3 + 3] Cycloaddition Reaction Promoted by Chiral Amine Salts
  作者：Aleksey I. Gerasyuto、Richard P. Hsung、Nadiya Sydorenko、Brian Slafer

  DOI：10.1021/jo050171s

  日期：2005.5.1

  A detailed account on chiral secondary amine salt promoted enantioselective intramolecular formal aza-[3 + 3] cycloadditions is described here for the first time. The dependence of enantioselectivity on the structural feature of these chiral amines is thoroughly investigated. This study also reveals a very interesting reversal of the stereochemistry in the respective cycloadducts obtained using C-1- and C-2-symmetric amine salts. In addition, the influence of solvents, counteranions, and temperatures on the enantioselectivity is described, and a unified mechanistic model based on experimental results as well as semiempirical calculations is proposed.
• Zur Halogenierung von 6-Halo-1,3-dimethyluracilen
  作者：Géza Szilágyi、Heinrich Wamhoff

  DOI：10.1055/s-1981-29565

  日期：——