2-amino-4-chloro-6-(piperidin-1-yl)pyrimidine-5-carbaldehyde | 865660-47-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-amino-4-chloro-6-(piperidin-1-yl)pyrimidine-5-carbaldehyde
• 英文别名: 2-amino-6-chloro-4-piperidinopyrimidine-5-carbaldehyde；2-amino-4-chloro-6-piperidin-1-ylpyrimidine-5-carbaldehyde
• CAS: 865660-47-5
• 化学式: C₁₀H₁₃ClN₄O
• mdl: MFCD04125346
• 分子量: 240.692
• InChiKey: NNTQTAQGKYJYSU-UHFFFAOYSA-N

物化性质

• 熔点：
  173-175 °C
• 沸点：
  497.1±55.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)
• 溶解度：
  34.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-4-chloro-6-(piperidin-1-yl)pyrimidine-5-carbaldehyde 在 一水合肼 作用下， 反应 0.02h， 以70%的产率得到4-piperidin-1-yl-1H-pyrazolo[3,4-d]pyrimidin-6-amine
  参考文献：
  名称：

  在无溶剂条件下由2-氨基-4,6-二氯嘧啶-5-甲醛通过微波辅助合成吡唑并[3,4- d ]嘧啶

  摘要：

  这里描述了在N 4-取代的2，4-二氨基-6-氯-5-甲醛醛3与肼的反应中微波诱导的吡唑并[3，4- d ]嘧啶4的合成。前体3是通过2-氨基-4，6-二氯嘧啶-5-甲醛2与脂族和芳族胺的单胺化反应制备的。与伯胺的反应时间相对短于仲胺。

  DOI：

  10.1016/j.tetlet.2008.03.090
• 作为产物：
  描述：

  哌啶 、 2-氨基-4,6-二氯嘧啶-5-甲醛 在 TEA 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以71%的产率得到2-amino-4-chloro-6-(piperidin-1-yl)pyrimidine-5-carbaldehyde
  参考文献：
  名称：

  在无溶剂条件下由2-氨基-4,6-二氯嘧啶-5-甲醛通过微波辅助合成吡唑并[3,4- d ]嘧啶

  摘要：

  这里描述了在N 4-取代的2，4-二氨基-6-氯-5-甲醛醛3与肼的反应中微波诱导的吡唑并[3，4- d ]嘧啶4的合成。前体3是通过2-氨基-4，6-二氯嘧啶-5-甲醛2与脂族和芳族胺的单胺化反应制备的。与伯胺的反应时间相对短于仲胺。

  DOI：

  10.1016/j.tetlet.2008.03.090

文献信息

• Six closely related 4,6-disubstituted 2-amino-5-formylpyrimidines: different ring conformations, polarized electronic structures, and hydrogen-bonded assembly in zero, one, two and three dimensions
  作者：Lina M. Acosta、Andrés F. Yepes、Alirio Palma、Justo Cobo、Christopher Glidewell

  DOI：10.1107/s0108270112051049

  日期：2013.2.15

  In each of ethylN-2-amino-5-formyl-6-[methyl(phenyl)amino]pyrimidin-4-yl}glycinate, C₁₆H₁₉N₅O₃, (I),N-2-amino-5-formyl-6-[methyl(phenyl)amino]pyrimidin-4-yl}glycinamide, C₁₄H₁₆N₆O₂, (II), and ethyl 3-amino-N-2-amino-5-formyl-6-[methyl(phenyl)amino]pyrimidin-4-yl}propionate, C₁₇H₂₁N₅O₃, (III), the pyrimidine ring is effectively planar, but in each of methylN-2-amino-6-[benzyl(methyl)amino]-5-formylpyrimidin-4-yl}glycinate, C₁₆H₁₉N₅O₃, (IV), ethyl 3-amino-N-2-amino-6-[benzyl(methyl)amino]-5-formylpyrimidin-4-yl}propionate, C₁₈H₂₃N₅O₃, (V), and ethyl 3-amino-N-[2-amino-5-formyl-6-(piperidin-4-yl)pyrimidin-4-yl]propionate, C₁₅H₂₃N₅O₃, (VI), the pyrimidine ring is folded into a boat conformation. The bond lengths in each of (I)–(VI) provide evidence for significant polarization of the electronic structure. The molecules of (I) are linked by paired N—H...N hydrogen bonds to form isolated dimeric aggregates, and those of (III) are linked by a combination of N—H...N and N—H...O hydrogen bonds into a chain of edge-fused rings. In the structure of (IV), molecules are linked into sheets by means of two hydrogen bonds, both of N—H...O type, in the structure of (V) by three hydrogen bonds, two of N—H...N type and one of C—H...O type, and in the structure of (VI) by four hydrogen bonds, all of N—H...O type. Molecules of (II) are linked into a three-dimensional framework structure by a combination of three N—H...O hydrogen bonds and one C—H...O hydrogen bond.

  在 N-2-氨基-5-甲酰基-6-[甲基(苯基)氨基]嘧啶-4-基}甘氨酸乙酯（C16H19N5O3，(I)）、N-2-氨基-5-甲酰基-6-[甲基(苯基)氨基]嘧啶-4-基}甘氨酰胺C14H16N6O2，(II) 和 3-氨基-N-2-氨基-5-甲酰基-6-[甲基（苯基）氨基]嘧啶-4-基}丙酸乙酯，C17H21N5O3，(III) 中，嘧啶环实际上是平面的、但在 N-2-氨基-6-[苄基（甲基）氨基]-5-甲酰基嘧啶-4-基}甘氨酸甲酯（C16H19N5O3，(IV)）、3-氨基-N-2-氨基-6-[苄基（甲基）氨基]-5-甲酰基嘧啶-4-基}丙酸乙酯（C18H23N5O3，(III)C18H23N5O3，(V) 和 3-氨基-N-[2-氨基-5-甲酰基-6-(哌啶-4-基)嘧啶-4-基]丙酸乙酯，C15H23N5O3，(VI)，嘧啶环折叠成舟形构象。(I)-(VI)中每个分子的键长都证明了电子结构的显著极化。(I)的分子通过成对的 N-H...N氢键连接形成孤立的二聚体，而(III)的分子则通过 N-H...N和 N-H...O氢键组合连接成边缘融合的环链。在（IV）的结构中，分子通过两个氢键（均为 N-H...O 型）连接成片状；在（V）的结构中，分子通过三个氢键（两个 N-H...N 型和一个 C-H...O 型）连接成片状；在（VI）的结构中，分子通过四个氢键（均为 N-H...O 型）连接成片状。(II)的分子通过三个 N-H...O 型氢键和一个 C-H...O 型氢键组合连接成三维框架结构。
• 2-Amino-4-(piperidin-1-yl)-11<i>H</i>-pyrimido[4,5-<i>b</i>][1,5]benzodiazepin-6-ium chloride monohydrate and 2-amino-4-[methyl(2-methylphenyl)amino]-11<i>H</i>-pyrimido[4,5-<i>b</i>][1,5]benzodiazepin-6-ium chloride–benzene-1,2-diamine (1/1): complex sheets generated by multiple hydrogen bonds
  作者：Jairo Quiroga、Jorge Trilleras、Justo Cobo、Christopher Glidewell

  DOI：10.1107/s0108270110006967

  日期：2010.4.15

  In each of 2-amino-4-(piperidin-1-yl)-11H-pyrimido[4,5-b][1,5] benzodiazepin-6-ium chloride monohydrate, C16H19N6+center dot-Cl-center dot H2O, (I), and 2-amino-4-[methyl(2-methylphenyl)amino]11H- pyrimido[4,5-b][1,5] benzodiazepin-6-ium chloride -benzene-1,2- diamine (1/1), C19H19N6+center dot Cl-center dot C6H8N2, (II), the seven-membered ring in the cation adopts a boat conformation. The pyrimidine ring in (II) adopts a twist-boat conformation, but the corresponding ring in (I) is essentially planar. The amino groups of the benzene-1,2-diamine component of (II) are both pyramidal. The independent components of (I) are linked into complex sheets by a combination of N-H center dot center dot center dot O, N-H center dot center dot center dot N, N-H center dot center dot center dot Cl and O-H center dot center dot center dot Cl hydrogen bonds. In the crystal structure of (II), one N-H center dot center dot center dot N hydrogen bond and six independent N-H center dot center dot center dot Cl hydrogen bonds combine to link the components into complex sheets.
• Microwave-assisted synthesis of pyrazolo[3,4-d]pyrimidines from 2-amino-4,6-dichloropyrimidine-5-carbaldehyde under solvent-free conditions
  作者：Jairo Quiroga、Jorge Trilleras、Braulio Insuasty、Rodrigo Abonía、Manuel Nogueras、Antonio Marchal、Justo Cobo

  DOI：10.1016/j.tetlet.2008.03.090

  日期：2008.5

  The microwave-induced synthesis of pyrazolo[3,4-d]pyrimidines 4 in the reaction of N4-substituted-2,4-diamino-6-chloro-5-carbaldehydes 3 with hydrazine is described here. Precursors 3 have been prepared by the mono-amination of 2-amino-4,6-dichloropyrimidine-5-carbaldehyde 2 with aliphatic and aromatic amines. The reaction times with primary amines were relatively shorter than for secondary amines

  这里描述了在N 4-取代的2，4-二氨基-6-氯-5-甲醛醛3与肼的反应中微波诱导的吡唑并[3，4- d ]嘧啶4的合成。前体3是通过2-氨基-4，6-二氯嘧啶-5-甲醛2与脂族和芳族胺的单胺化反应制备的。与伯胺的反应时间相对短于仲胺。