2-叔丁基-4,6-二羟基嘧啶 | 18378-79-5

• 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-叔丁基-4,6-二羟基嘧啶
• 英文名称: 4,6-dihydroxy-2-tert-butyl-pyrimidine
• 英文别名: 2-t-butylpyrimidine-4,6-diol；2-tert-butyl-1H-pyrimidine-4,6-dione；2-tert-butyl-4,6-dihydroxypyrimidine；2-tert-butylpyrimidine-4,6-diol；2-t-Butyl-4,6-dihydroxypyrimidin；2-tert-butyl-4-hydroxy-1H-pyrimidin-6-one
• CAS: 18378-79-5
• 化学式: C₈H₁₂N₂O₂
• 分子量: 168.195
• InChiKey: HRVWBFSYFICPAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  2-叔丁基-4,6-二羟基嘧啶 在 三氯氧磷 作用下， 反应 5.0h， 以0.41 g的产率得到2-tert-butyl-4,6-dichloropyrimidine
  参考文献：
  名称：

  Structure−Activity Studies on a Series of a 2-Aminopyrimidine-Containing Histamine H₄ Receptor Ligands

  摘要：

  A series of 2-aminopyrimidines was synthesized as ligands of the histamine H-4 receptor (H4R). Working in part from a pyrimidine hit that was identified in an HTS campaign, SAR studies were carried out to optimize the potency, which led to compound 3,4-tert-butyl-6-(4-methylpiperazin-1-yl)pyrimidin-2-ylamine. We further studied this compound by systematically modifying the core pyrimidine moiety, the methylpiperazine at position 4, the NH2 at position 2, and positions 5 and 6 of the pyrimidine ring. The pyrimidine 6 position benefited the most from this optimization, especially in analogs in which the 6-tert-butyl was replaced with aromatic and secondary amine moieties. The highlight of the optimization campaign was compound 4, 4-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]benzonitrile, which was potent in vitro and was active as an anti-inflammatory agent in an animal model and had antinociceptive activity in a pain model, which supports the potential of H4R antagonists in pain.

  DOI：

  10.1021/jm8005959
• 作为产物：
  描述：

  2,2-二甲基丙亚胺盐酸 、 丙二酸二甲酯 在 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 19.25h， 生成 2-叔丁基-4,6-二羟基嘧啶
  参考文献：
  名称：

  Structure−Activity Studies on a Series of a 2-Aminopyrimidine-Containing Histamine H₄ Receptor Ligands

  摘要：

  A series of 2-aminopyrimidines was synthesized as ligands of the histamine H-4 receptor (H4R). Working in part from a pyrimidine hit that was identified in an HTS campaign, SAR studies were carried out to optimize the potency, which led to compound 3,4-tert-butyl-6-(4-methylpiperazin-1-yl)pyrimidin-2-ylamine. We further studied this compound by systematically modifying the core pyrimidine moiety, the methylpiperazine at position 4, the NH2 at position 2, and positions 5 and 6 of the pyrimidine ring. The pyrimidine 6 position benefited the most from this optimization, especially in analogs in which the 6-tert-butyl was replaced with aromatic and secondary amine moieties. The highlight of the optimization campaign was compound 4, 4-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]benzonitrile, which was potent in vitro and was active as an anti-inflammatory agent in an animal model and had antinociceptive activity in a pain model, which supports the potential of H4R antagonists in pain.

  DOI：

  10.1021/jm8005959

文献信息

• Methylation of Some Deprotonated Sterically Hindered Pyrimidin-4-ols
  作者：RF Evans、GP Savage

  DOI：10.1071/ch9920463

  日期：——

  Anions derived from t-butyl-substituted pyrimidin-4-ols were methylated with iodomethane . The site of methylation was determined by proton-coupled 13C n.m.r. and the relative proportions of isomers were determined by 1H n.m.r. A t-butyl substituent ortho to a ring nitrogen markedly reduced the propensity for methylation at that nitrogen to the point where O-methylation, uncommon under these conditions, was observed.

  用碘甲烷将 t-丁基取代的嘧啶-4-醇中的阴离子甲基化。通过质子耦合 13C n.m.r.确定了甲基化的位点，并通过 1H n.m.r.确定了异构体的相对比例。环氮正交的叔丁基取代基明显降低了该氮的甲基化倾向，以至于观察到在这些条件下不常见的 O-甲基化。
• Pesticidal pyrimidinyl (thiono) (thio)-phosphoric (phosphonic)acid
  申请人：Bayer Aktiengesellschaft

  公开号：US05064818A1

  公开（公告）日：1991-11-12

  Insecticidal, acaricidal and nematocidal pyrimidinyl(thiono)(thio)-phosphoric(phosphonic) acid (amide) esters of the formula ##STR1## in which R represents hydrogen, or represents an optionally substituted radical selected from the group consisting of alkyl, alkoxy, alkylthio, dialkylamino, cycloalkyl and aryl, R.sup.1 represents hydrogen, aklyl or halogen, R.sup.2 represents alkyl, R.sup.3 represents alkyl, alkoxy, alkylthio, amino, alkylamino, dialkylamino or aryl and X represents oxygen or sulphur.

  式子如下：##STR1## 其中，R代表氢，或代表选自烷基，烷氧基，烷基硫基，二烷基氨基，环烷基和芳基的可选取代基团；R.sup.1代表氢，烷基或卤素；R.sup.2代表烷基；R.sup.3代表烷基，烷氧基，烷基硫基，氨基，烷基氨基，二烷基氨基或芳基；X代表氧或硫。这些化合物具有杀虫，杀螨和杀线虫的作用。
• 4-AMINOPYRIMIDINE DERIVATIVES AS HISTAMINE H4 RECEPTOR ANTAGONISTS
  申请人：Carceller González Elena

  公开号：US20110039817A1

  公开（公告）日：2011-02-17

  4-Aminopyrimidine derivatives of formula (I) that are useful as histamine H4 receptor antagonists.

  式(I)的4-氨基嘧啶衍生物可用作组胺H4受体拮抗剂。
• Thionophosphonsäureester
  申请人：BAYER AG

  公开号：EP0279259A1

  公开（公告）日：1988-08-24

  Die Erfindung betrifft die neuen O-(6-Alkoxy-2-tert.-­butyl-pyrimidin-4-yl)-O-methyl-thionoethanphosphonsäure­diester der allgemeinen Formel (I) in welcher R für Alkyl mit 1 bis 4 Kohlenstoffatomen oder für Cycloalkyl mit 3 oder 4 Kohlenstoffatomen steht, welche als Schädlingsbekämpfungsmittel verwendet werden können.

  本发明涉及通式(I)的新型 O-(6-烷氧基-2-叔丁基嘧啶-4-基)-O-甲基-硫代乙烷膦酸二酯类。 其中 R 代表 1 至 4 个碳原子的烷基或 3 或 4 个碳原子的环烷基，可用作农药。
• Pyrimidinyl(thiono)(thiol)-phosphor(phosphon)säure(amid)ester
  申请人：BAYER AG

  公开号：EP0395968A1

  公开（公告）日：1990-11-07

  Die Erfindung betrifft neue Pyrimidin(thiono)(thiol)-phosphor(phosphon)säure(amid)ester der allgemeinen Formel (I) in welcher R für Wasserstoff, oder für einen gegebenenfalls substituierten Rest der Reihe Alkyl, Alkoxy, Alkylthio, Dialkylamino, Cycloalkyl und Aryl steht, R1 für Wasserstoff, Alkyl oder Halogen steht, R2 für Alkyl steht, R3 für Alkyl, Alkoxy, Alkylthio, Amino, Alkylamino, Dialkylamino oder Aryl steht und X für Sauerstoff oder Schwefel steht. welche als Schädlingsbekämpfungsmittel verwendet werden können.

  本发明涉及通式(I)的新型嘧啶(硫)(硫醇)-磷(膦)酸(酰胺)酯 其中 R 代表氢，或烷基、烷氧基、烷硫基、二烷基氨基、环烷基和芳基系列中的任选取代基、 R1 是氢、烷基或卤素、 R2 是烷基 R3 是烷基、烷氧基、烷硫基、氨基、烷基氨基、二烷基氨基或芳基，以及 X 是氧或硫。 可用作杀虫剂。