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2,4-diamine-1,3,5-triazine compound, preparation method and application thereof

A compound and triazine technology, applied in the field of 2,4-diamine-1,3,5-triazine compounds, can solve the problems of difficult control of reaction conditions, complicated steps, poor yield, etc. Industrial application prospects, easy operation, low cost effect

Active Publication Date: 2016-08-10
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above methods have disadvantages such as the use of highly toxic reagents, expensive catalysts or ligands, uneasy control of reaction conditions, cumbersome steps, and poor yields, and are subject to certain limitations during use.

Method used

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  • 2,4-diamine-1,3,5-triazine compound, preparation method and application thereof
  • 2,4-diamine-1,3,5-triazine compound, preparation method and application thereof
  • 2,4-diamine-1,3,5-triazine compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Preparation of 2-amino-1,3,5-triazine compound (I)

[0029] Taking 2-amino-4-dimethylamino-6-phenyl-1,3,5-triazine as an example, its preparation method is:

[0030] Mix methyl benzoate (react IV, 0.1362 g, 1 mmol), metformin hydrochloride (react V, 0.0662 g, 0.4 mmol), sodium methoxide (0.0540 g, 1 mmol) in methanol (10 mL), and Reaction under the condition of (25°C), TLC tracking monitoring, reaction for 12h, after that, the reaction solution was evaporated to remove the solvent, 10mL of water was added, filtered, and the filter cake was recrystallized with methanol to obtain white crystals, which were dried to obtain 2-amino-4-dimethylamine 0.0563 g of phenyl-6-phenyl-1,3,5-triazine, yield 65.4%.

Embodiment 2～9

[0031] Examples 2-9 Preparation of 2-amino-1,3,5-triazine compound (I)

[0032] The following Examples 2-9 were prepared according to the method described in Example 1, wherein different reaction substrates and their feeding amounts, different reaction products and their yields are listed in Table 1.

[0033] Reaction substrate and its charging amount in the embodiment 2~9 of table 1, reaction product and its productive rate

[0034]

Embodiment 10

[0035] Embodiment 10: the preparation of compound (III-1)

[0036] Add 2-amino-4-dimethylamino-6-phenyl-1,3,5-triazine (0.1076g, 0.50mmol), p-methoxy iodobenzene (0.1170g, 0.50mmol) into the reaction vessel , cuprous iodide (0.0285g, 0.15mmol), potassium carbonate (0.1380g, 1.00mmol), N,N'-dimethylethylenediamine (DMEDA, 0.0396g, 0.45mmol) and solvent acetonitrile (3mL), Reflux for 10 hours. Cool after the reaction, add ammonia water 4mL, stir for 5 minutes, add saturated NaCl aqueous solution (20mL), extract with ethyl acetate (20mL×3), combine organic layers, concentrate, column chromatography (eluent is petroleum ether: Ethyl acetate=5:1, v:v), collect R f The eluate with a value of 0.4-0.45 (monitored by TLC, the developing solvent is the same as the eluent), the solvent was distilled off under reduced pressure, and dried to obtain 0.1222 g of the target compound (III-1), with a yield of 76.0%. 1 H NMR (500MHz, CDCl 3 ):δ8.44-8.42(m,2H),7.58(d,J=9.0Hz,2H),7.53-7.46(m,3...

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Abstract

The invention provides a 2,4-diamine-1,3,5-triazine compound represented as the formula (III). A preparation method includes the following steps: adding compounds represented as the formulas (I) and (II), a metal copper catalyst, a ligand, an alkaline substance and a solvent into a reaction container, stirring the reactants to perform a reaction at 80-140 DEG C for 6-14 h and performing after treatment to the reaction liquid to obtain the compound (III). The preparation method has mild reaction conditions and convenient operations, is low in cost and has wide industrial application prospect. The 2,4-diamine-1,3,5-triazine compound has certain antibacterial activity and can be used for preparing antibacterial medicines and agents, lays fundament for screening and developing new medicines and has great practical value.

Description

(1) Technical field [0001] The invention relates to a 2,4-diamine-1,3,5-triazine compound and a preparation method and application thereof. (2) Background technology [0002] 2,4-disubstituted amino-1,3,5-triazine compounds have a variety of pharmacological activities, such as antibacterial activity, anti-trypanosomal activity, anti-retroviral activity, cytotoxic activity and anti-angiogenesis activity, etc. . At present, the synthesis methods of such compounds mainly include the following: (1) prepared from aryl isothiocyanate, guanidine and amidine under the catalysis of mercuric chloride; (2) prepared from bromobenzene, substituted aniline, diethyl Amine and cyanuric chloride are prepared through multi-step reaction under the catalysis of sodium cyanoborohydride; (3) prepared by substitution reaction of 2,4-dichloro-1,3,5-triazine and amine. The above methods have disadvantages such as the use of highly toxic reagents, expensive catalysts or ligands, difficult control o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/18C07D409/04A61P31/04
CPCC07D251/18C07D409/04
Inventor 崔冬梅李进京吴空张辰
Owner ZHEJIANG UNIV OF TECH
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