2-氨基-4-氯-6-甲基-5-炔丙基嘧啶 | 132938-37-5

• 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-氨基-4-氯-6-甲基-5-炔丙基嘧啶
• 中文别名: 4-氯-6-甲基-5-(2-丙炔)-2-嘧啶胺
• 英文名称: 2-Amino-4-chloro-6-methyl-5-(2-propynyl)pyrimidine
• 英文别名: 4-Chloro-6-methyl-5-(2-propynyl)-2-pyrimidinamine；4-chloro-6-methyl-5-prop-2-ynylpyrimidin-2-amine
• CAS: 132938-37-5
• 化学式: C₈H₈ClN₃
• mdl: MFCD09746373
• 分子量: 181.625
• InChiKey: QWBJSLGKMVRROO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基-4-氯-6-甲基-5-炔丙基嘧啶 在 potassium carbonate 、 氯乙酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 31.0h， 生成 6-Methyl-5-(2-propynyl)-2,4(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  2,4-Dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine: a potential synthon for 5-(1-o-carboranylmethyl)pyrimidines

  摘要：

  The synthesis of 2,4-dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine is described. Synthetically, this novel o-carboranyl pyrimidine is approached from ethyl 2-acetyl-4-pentynoate through alkylation of ethyl acetoacetate with propargyl bromide and subsequent condensation with thiourea to yield 6-methyl-5-(2-propynyl)-2-thio-4(1H,3H)-pyrimidinone. Hydrolysis of the 2-thione and chlorination with POCl3 gives 2,4-dichloro-6-methyl-5(2-propynyl)pyrimidine. Gentle refluxing of this product with B10H14/CH3CN in toluene yields the target, 2,4-dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine, a potential synthon for a variety of 2,4-substituted 5-(1-o-carboranylmethyl)-6-methylpyrimidines and/or the corresponding nido-undecaborates.

  DOI：

  10.1021/jo00007a026
• 作为产物：
  描述：

  ethyl 2-acetylpent-4-ynoate 在 三氯氧磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 2-氨基-4-氯-6-甲基-5-炔丙基嘧啶
  参考文献：
  名称：

  2,4-Dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine: a potential synthon for 5-(1-o-carboranylmethyl)pyrimidines

  摘要：

  The synthesis of 2,4-dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine is described. Synthetically, this novel o-carboranyl pyrimidine is approached from ethyl 2-acetyl-4-pentynoate through alkylation of ethyl acetoacetate with propargyl bromide and subsequent condensation with thiourea to yield 6-methyl-5-(2-propynyl)-2-thio-4(1H,3H)-pyrimidinone. Hydrolysis of the 2-thione and chlorination with POCl3 gives 2,4-dichloro-6-methyl-5(2-propynyl)pyrimidine. Gentle refluxing of this product with B10H14/CH3CN in toluene yields the target, 2,4-dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine, a potential synthon for a variety of 2,4-substituted 5-(1-o-carboranylmethyl)-6-methylpyrimidines and/or the corresponding nido-undecaborates.

  DOI：

  10.1021/jo00007a026

文献信息

• 2,4-Dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine: a potential synthon for 5-(1-o-carboranylmethyl)pyrimidines
  作者：Robert C. Reynolds、Todd W. Trask、W. David Sedwick

  DOI：10.1021/jo00007a026

  日期：1991.3

  The synthesis of 2,4-dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine is described. Synthetically, this novel o-carboranyl pyrimidine is approached from ethyl 2-acetyl-4-pentynoate through alkylation of ethyl acetoacetate with propargyl bromide and subsequent condensation with thiourea to yield 6-methyl-5-(2-propynyl)-2-thio-4(1H,3H)-pyrimidinone. Hydrolysis of the 2-thione and chlorination with POCl3 gives 2,4-dichloro-6-methyl-5(2-propynyl)pyrimidine. Gentle refluxing of this product with B10H14/CH3CN in toluene yields the target, 2,4-dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine, a potential synthon for a variety of 2,4-substituted 5-(1-o-carboranylmethyl)-6-methylpyrimidines and/or the corresponding nido-undecaborates.