2-amino-4,6-dimethylpyrimidine-fumaric acid co-crystal material and preparation method, application thereof

Abstract

The application belongs to the field of co-crystals and provides a 2-amino-4,6-dimethylpyrimidine-fumaric acid co-crystal material, the 2-amino-4,6-dimethylpyrimidine-fumaric acid co-crystal material is a colorless transparent crystal prepared by dissolving 2-amino-4,6-dimethylpyrimidine and fumaric acid in an organic solvent and then using a crystallization method, and the pyrimidine-organic acid co-crystal material has fluorescence performance. The co-crystal material has good fluorescence performance, especially under light with a wavelength of 365 nm, presents light yellow fluorescence, and is expected to be applied in the fields of fluorescence detection and optoelectronic devices.

Description

Technical Field

[0001] This invention belongs to the field of crystal and its application technology, and particularly relates to a 2-amino-4,6-dimethylpyrimidine and fumaric acid eutectic material, its preparation method and application. Background Technology

[0002] Currently, pyrimidine compounds and organic acids are used to construct organic cocrystal materials via hydrogen bonding. However, these cocrystal materials are usually drug cocrystals and are commonly used in the pharmaceutical field. Summary of the Invention

[0003] This invention provides a pyrimidine-organic acid eutectic material, its preparation method, and its application. This eutectic material has good fluorescence properties, especially exhibiting pale yellow fluorescence under 365nm light, and is expected to be applied in the fields of fluorescence detection and optoelectronic devices.

[0004] To achieve the above objectives, the technical solution of the present invention is as follows: The first aspect of this application provides a 2-amino-4,6-dimethylpyrimidine-fumaric acid co-crystal material, wherein the 2-amino-4,6-dimethylpyrimidine-fumaric acid co-crystal material is a colorless and transparent crystal prepared by crystallization after dissolving 2-amino-4,6-dimethylpyrimidine and fumaric acid in an organic solvent, and the pyrimidine-organic acid co-crystal material has fluorescent properties.

[0005] Specifically, the 2-amino-4,6-dimethylpyrimidine-fumaric acid eutectic material exhibits pale yellow fluorescence under 365 nm light illumination.

[0006] The second aspect of this application provides a method for preparing a eutectic material of 2-amino-4,6-dimethylpyrimidine and fumaric acid, comprising the following steps: S1: Mix 2-amino-4,6-dimethylpyrimidine and fumaric acid in a predetermined ratio and place them in a reaction vessel; S2: Add organic solvent to the reaction vessel, heat to 70 °C, stir, filter, and take the clear solution; S3: Crystallize using the crystallization method to obtain colorless and transparent crystals.

[0007] Preferably, the molar ratio of the pyrimidine derivative to the dicarboxylic acid is 1:0.5-2.

[0008] Preferably, the molar ratio of the pyrimidine derivative to the dicarboxylic acid is 1:1.

[0009] Preferably, the organic solvent is any one of methanol, ethanol, or isopropanol.

[0010] Preferably, in step S3, a cooling crystallization method or a solvent evaporation method is used for crystallization. In order to improve the crystal quality, a trace amount of seed crystals can also be added as seed crystals to induce crystallization. The cooling crystallization method specifically involves naturally cooling the clear solution or cooling it with water or ice water to allow crystals to precipitate. The solvent evaporation method specifically involves slowly evaporating the solvent from the clear solution at room temperature.

[0011] The third aspect of this application provides an application of a eutectic material of 2-amino-4,6-dimethylpyrimidine and fumaric acid in the fields of fluorescence detection or optoelectronic devices.

[0012] Because the present invention adopts the above technical solution, it has the following advantages and positive effects compared with the prior art: This invention successfully prepared a 2-amino-4,6-dimethylpyrimidine-fumaric acid co-crystal material with a well-defined structure and stable fluorescence performance by precisely controlling the molar ratio of raw materials, solvent type, dissolution temperature, and crystallization method, thus expanding its application in the field of fluorescent materials. Under 365 nm illumination, the sample exhibited pale yellow fluorescence, indicating that the 2-amino-4,6-dimethylpyrimidine-fumaric acid co-crystal possesses stable fluorescence properties, making it suitable for fluorescence detection and optoelectronic devices. Attached Figure Description

[0013] Figure 1 This is a process flow diagram of the fabrication process of the 2-amino-4,6-dimethylpyrimidine and fumaric acid eutectic material according to an embodiment of the present invention; Figure 2 The atomic structure of the 2-amino-4,6-dimethylpyrimidine and fumaric acid eutectic material of Example 1 of the present invention is shown below. Figure 3 The XRD diffraction pattern of the 2-amino-4,6-dimethylpyrimidine and fumaric acid eutectic material of Example 1 of the present invention is shown below. Figure 4 The UV-Vis absorption spectrum of the 2-amino-4,6-dimethylpyrimidine and fumaric acid eutectic material of Example 1 of the present invention is shown in (a) and (b) is shown in (b). Detailed Implementation

[0014] 2-Amino-4,6-dimethylpyrimidine is a common nitrogen-containing heterocyclic compound widely used in drug synthesis and pesticide preparation. Fumaric acid, as an organic acid, has excellent hydrogen bond donor capabilities and is often used to construct organic cocrystal materials. However, the relationship between drug cocrystals and fluorescence properties has not yet been systematically studied, limiting the application of drug cocrystals in the field of fluorescent materials.

[0015] The following detailed description, in conjunction with the accompanying drawings and specific embodiments, provides a further detailed explanation of the 2-amino-4,6-dimethylpyrimidine-fumaric acid eutectic material, its preparation method, and its applications. The advantages and features of the present invention will become clearer from the following description. Example 1

[0016] like Figure 1 A method for preparing a 2-amino-4,6-dimethylpyrimidine-fumaric acid eutectic material, comprising the following steps: (1) Weigh 10 mmol of 2-amino-4,6-dimethylpyrimidine and 10 mmol of fumaric acid and place them in a reaction vessel; (2) Add 250 mL of methanol as a solvent, heat to 70 °C, and stir until the solution is completely clear; (3) Filter while hot to remove insoluble impurities; (4) The solvent in the filtrate was slowly evaporated at room temperature. After about one week, colorless and transparent blocky crystals were obtained.

[0017] Structural characterization: Single-crystal diffraction data were collected using a Rigaku XtaLAB Synergy-R / DW single-crystal X-ray diffractometer with Mo-Kα rays (λ = 0.71073 Å). The molecular structure of the eutectic was obtained using SHELXTL software. Figure 2 As shown. Structural analysis reveals that 2-amino-4,6-dimethylpyrimidine and fumaric acid form a 1:1 eutectic structure through hydrogen bonding.

[0018] Powder X-ray diffraction (PXRD) analysis: A Rigaku D / MAX 2000 PC X-ray diffractometer was used at room temperature with a 2θ range of 5°–50°, a step size of 0.02°, and a scan rate of 10° / min. The resulting PXRD patterns are shown below. Figure 3 As shown, the results are highly consistent with the simulated single-crystal structure, indicating that the product is a pure phase.

[0019] Fluorescence performance test: Fluorescence spectroscopy of the powder sample was measured using a Shimadzu RF-6000 fluorescence spectrophotometer. Under 365 nm illumination, the sample exhibited pale yellow fluorescence (…). Figure 4 (a)). Excitation and emission spectra as follows: Figure 4 As shown in (a,b), this material has good fluorescence properties and is suitable for fluorescence detection and optoelectronic devices. Example 2

[0020] A method for preparing a 2-amino-4,6-dimethylpyrimidine-fumaric acid eutectic material, comprising the following steps: (1) Weigh 20 mmol of 2-amino-4,6-dimethylpyrimidine and 10 mmol of fumaric acid and place them in a reaction vessel; (2) Add 250 mL of ethanol as a solvent, heat to 70 °C, and stir until the solution is completely clear; (3) Filter while hot to remove insoluble impurities; (4) The solvent in the filtrate was slowly evaporated at room temperature. After about one week, colorless and transparent blocky crystals were obtained. Example 3

[0021] A method for preparing a 2-amino-4,6-dimethylpyrimidine-fumaric acid eutectic material, comprising the following steps: (1) Weigh 10 mmol of 2-amino-4,6-dimethylpyrimidine and 20 mmol of fumaric acid and place them in a reaction vessel; (2) Add 250 mL of isopropanol as a solvent, heat to 70 °C, and stir until the solution is completely clear; (3) Filter while hot to remove insoluble impurities; (4) The solvent in the filtrate was slowly evaporated at room temperature. After about one week, colorless and transparent blocky crystals were obtained.

[0022] The embodiments of the present invention have been described in detail above with reference to the accompanying drawings, but the present invention is not limited to the above embodiments. Even if various changes are made to the present invention, if these changes fall within the scope of the claims of the present invention and their equivalents, they shall still fall within the protection scope of the present invention.

Claims

1. A 2-amino-4,6-dimethylpyrimidine-fumaric acid eutectic material, characterized in that, The 2-amino-4,6-dimethylpyrimidine-fumaric acid eutectic material is a colorless and transparent crystal prepared by crystallization after dissolving 2-amino-4,6-dimethylpyrimidine and fumaric acid in an organic solvent. The pyrimidine-organic acid eutectic material has fluorescent properties.

2. The 2-amino-4,6-dimethylpyrimidine-fumaric acid eutectic material according to claim 1, characterized in that, The 2-amino-4,6-dimethylpyrimidine-fumaric acid eutectic material exhibits pale yellow fluorescence under 365 nm light illumination.

3. A method for preparing the 2-amino-4,6-dimethylpyrimidine and fumaric acid eutectic material as described in claim 1 or 2, characterized in that, Includes the following steps: S1: Mix 2-amino-4,6-dimethylpyrimidine and fumaric acid in a predetermined ratio and place them in a reaction vessel; S2: Add organic solvent to the reaction vessel, heat to 70 °C, stir, filter, and take the clear solution; S3: Crystallize using the crystallization method to obtain colorless and transparent crystals.

4. The method for preparing the 2-amino-4,6-dimethylpyrimidine and fumaric acid eutectic material according to claim 3, characterized in that, The molar ratio of the pyrimidine derivative to the dicarboxylic acid is 1:0.5-2.

5. The method for preparing the 2-amino-4,6-dimethylpyrimidine and fumaric acid eutectic material according to claim 4, characterized in that, The molar ratio of the pyrimidine derivative to the dicarboxylic acid is 1:

1.

6. The method for preparing the 2-amino-4,6-dimethylpyrimidine and fumaric acid eutectic material according to claim 3, characterized in that, The organic solvent is any one of methanol, ethanol, or isopropanol.

7. The method for preparing the 2-amino-4,6-dimethylpyrimidine and fumaric acid eutectic material according to claim 3, characterized in that, In step S3, either cooling crystallization or solvent evaporation crystallization is used.

8. The application of the 2-amino-4,6-dimethylpyrimidine and fumaric acid eutectic material as described in claim 1 in the field of fluorescence detection or optoelectronic devices.

Images