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Synthesis process of thiazole substituted pyrimidine compound

A synthesis process and compound technology, which is applied in the field of synthesis of polybasic substituted pyrimidines in pharmaceutical intermediates, can solve the problems of low yield of target products and multiple by-products, and achieve improved selectivity and controllability of operation, high yield synthesis , produce controllable effects

Inactive Publication Date: 2018-06-08
韩邦森
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Poly-substituted pyrimidine compounds, especially thiazole-substituted pyrimidine compounds, are usually prepared by condensation of unsaturated carbonyl derivatives and amidine compounds under transition metal catalyzed conditions such as copper and silver, but this synthesis method will generate more By-products, resulting in lower yields of the target product

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  • Synthesis process of thiazole substituted pyrimidine compound
  • Synthesis process of thiazole substituted pyrimidine compound
  • Synthesis process of thiazole substituted pyrimidine compound

Examples

Experimental program
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Effect test

Embodiment 1

[0039] A synthesis process for thiazole-substituted pyrimidine compounds represented by the following formula (1), comprising the following steps:

[0040] Thiazole ring closure reaction

[0041] The compound represented by the following formula (2) (6g, 1.2mol) and the compound represented by the following formula (3) (6.5g, 1.7mol) in the accelerator bistrifluoromethanesulfonylimide silver salt (0.9g, 0.6mol) , catalyst β-cyclodextrin (1g, 1.2mol), co-catalyst phenylphosphine gold chloride (0.15g, 0.24mol), in N,N-dimethylformamide (DMF) (40ml) and In 1,4-dioxane (13.5ml) mixed solvent, magnetically stirred for 4 hours, thiazole ring closure reaction occurred, and the reaction was completed by TLC detection;

[0042] pyrimidine cyclization reaction

[0043] The reaction system after the thiazole ring closure reaction was first acetylated, and then the compound N,N-dimethylformamide dimethyl acetal (DMF-DMA) (7.5g, 1.2mol), heated to 105°C under the action of additive guan...

Embodiment 2

[0051] A synthesis process for thiazole-substituted pyrimidine compounds represented by the following formula (1), comprising the following steps:

[0052] Thiazole ring closure reaction

[0053]The compound represented by the following formula (2) (6g, 1.2mol) and the compound represented by the following formula (3) (6.9g, 1.8mol) in the accelerator bistrifluoromethanesulfonimide silver salt (1.05g, 0.96mol) , catalyst β-cyclodextrin (1.08g, 1.4mol), co-catalyst phenylphosphine gold chloride (0.22g, 0.36mol), in N,N-dimethylformamide (DMF) (45ml) In a mixed solvent with 1,4-dioxane (15ml), magnetically stir the reaction for 4 hours, a thiazole ring closure reaction occurs, and the reaction is completed by TLC detection;

[0054] pyrimidine cyclization reaction

[0055] The reaction system after the thiazole ring closure reaction is first acetylated, and then the compound N,N-dimethylformamide dimethyl acetal (DMF-DMA) (8g, 1.43 mol), heated to 120°C under the action of ad...

Embodiment 3

[0063] A synthesis process for thiazole-substituted pyrimidine compounds represented by the following formula (1), comprising the following steps:

[0064] Thiazole ring closure reaction

[0065] The compound represented by the following formula (2) (6g, 1.2mol) and the compound represented by the following formula (3) (7.1g, 2.1mol) in the accelerator bistrifluoromethanesulfonimide silver salt (1g, 0.84mol), Under the action of catalyst β-cyclodextrin (1.2g, 1.5mol) and cocatalyst phenylphosphine gold chloride (0.26g, 0.43mol), in N,N-dimethylformamide (DMF) (45ml) and In 1,4-dioxane (15ml) mixed solvent, magnetically stirred for 4 hours, thiazole ring closure reaction occurred, and TLC detected that the reaction was complete;

[0066] pyrimidine cyclization reaction

[0067] The reaction system after the thiazole ring closure reaction was first acetylated, and then the compound N,N-dimethylformamide dimethyl acetal (DMF-DMA) (11.2g, 2.16mol), heated to 140°C under the act...

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Abstract

The invention discloses a synthesis process of a thiazole substituted pyrimidine compound shown in a formula (I). The synthesis process comprises a thiazole cyclization reaction and a pyrimidine cyclization reaction. The synthesis process disclosed by the invention adopts unique reactants and a comprehensive reaction system, so that high-yield synthesis of the thiazole substituted pyrimidine compound is realized, reaction selectivity and operation controllability are improved, production of the thiazole substituted pyrimidine compound is more controllable, and the new sought synthesis processof the thiazole substituted pyrimidine compound is highly significant to an economic technology of the thiazole substituted pyrimidine compound. (The formula (I) is described in the specification).

Description

Technical field [0001] The invention relates to the technical field of synthesizing polyradical-substituted pyrimidines as pharmaceutical intermediates, in particular to a synthesis process for thiazole-substituted pyrimidines. Background technique [0002] Polysubstituted pyrimidines are an important class of nitrogen-heterocyclic organic compounds. Their skeletons not only widely exist in natural products and active pharmaceutical molecules, but also can be used as advanced materials and metal ligands, and are also important intermediates in organic synthesis. [0003] At present, polysubstituted pyrimidine compounds are widely used in biomedicine, for example: thiazole-substituted pyrimidine can be used as a melanoma drug; mepimethine can be used as an antipsychotic drug; Thereby interfering with the normal metabolism of folic acid of Plasmodium, it is effective for Plasmodium falciparum and Plasmodium vivax prophase erythrocytes, and can be used as etiological prophylaxi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04
CPCC07D417/04
Inventor 韩邦森
Owner 韩邦森
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