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Pyrrolo[3,2-d] pyrimidine compound, and preparation method and purification method thereof

A compound, 2-d technology, applied to pyrrolopyrimidine compound materials, preparation method and its purification, pyrrolo [3, can solve the problems of synthesis that are rarely reported, and achieve easy access to reaction reagents, good application prospects, and structure novel effect

Inactive Publication Date: 2015-02-18
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, there are few reports on pyrrolo[3,2-d]pyrimidines, especially the synthesis of compounds with substituents at the 5-position of the pyrrole ring and aniline substitution at the 6-position of the pyrimidine ring.

Method used

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  • Pyrrolo[3,2-d] pyrimidine compound, and preparation method and purification method thereof
  • Pyrrolo[3,2-d] pyrimidine compound, and preparation method and purification method thereof
  • Pyrrolo[3,2-d] pyrimidine compound, and preparation method and purification method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 1mmol N 4 -Phenyl-4,5-diamino-6-iodo-pyrimidine, 0.05mmol bis(triphenylphosphine)palladium dichloride, 0.05mmol cuprous iodide, 10mmol triethylamine, and 5ml tetrahydrofuran were added to the two-necked flask, Under the protection of nitrogen and 0°C, slowly add 1.5mmol trimethylsilylacetylene dropwise, keep the reaction at 0°C for 10min, TLC detects that the reaction of the raw materials is complete, add water to the mixture to quench the reaction, add ethyl acetate for extraction, and combine the organic layers , and dried with anhydrous sodium sulfate, and the residue obtained by rotary evaporation to remove the solvent was subjected to silica gel column chromatography, petroleum ether: ethyl acetate = 5:1 elution, to obtain a white solid product, which was dissolved in tetrahydrofuran, at 0 Slowly add 1 mmol of tetrabutylammonium fluoride in batches at °C. After the addition is complete, TLC detects that the reaction is complete, and the solvent is removed by rotary...

Embodiment 2

[0036] 1mmol N 4-(3-chlorophenyl)-4,5-diamino-6-iodopyrimidine, 0.05mmol bis(triphenylphosphine)palladium dichloride, 0.05mmol cuprous iodide, 10mmol triethylamine, 5ml tetrahydrofuran were added In the two-neck flask, under nitrogen protection and 0°C, slowly add 1.5mmol trimethylsilylacetylene dropwise, keep at 0°C for 10 minutes, TLC detects that the reaction of the raw materials is complete, add water to the mixture to quench the reaction, add ethyl acetate to extract , the organic layers were combined, and dried with anhydrous sodium sulfate, and the residue obtained by rotary evaporation to remove the solvent was subjected to silica gel column chromatography, petroleum ether: ethyl acetate = 5: 1 elution, and a light yellow solid product was obtained, which was dissolved in In tetrahydrofuran, 1 mmol tetrabutylammonium fluoride was slowly added in batches at 0°C. After the addition was complete, the reaction was complete as detected by TLC, and the solvent was removed by...

Embodiment 3

[0040] 1mmol N 4 -(4-chlorophenyl)-4,5-diamino-6-iodopyrimidine, 0.05mmol bis(triphenylphosphine)palladium dichloride, 0.05mmol cuprous iodide, 10mmol triethylamine, 5ml tetrahydrofuran were added In the two-neck flask, under nitrogen protection and 0°C, slowly add 1.5mmol trimethylsilylacetylene dropwise, keep at 0°C for 10 minutes, TLC detects that the reaction of the raw materials is complete, add water to the mixture to quench the reaction, add ethyl acetate to extract , the organic layers were combined, and dried with anhydrous sodium sulfate, and the residue obtained by rotary evaporation to remove the solvent was subjected to silica gel column chromatography, petroleum ether: ethyl acetate = 5: 1 elution, and a light yellow solid product was obtained, which was dissolved in In tetrahydrofuran, 1 mmol tetrabutylammonium fluoride was slowly added in batches at 0°C. After the addition was complete, the reaction was complete as detected by TLC, and the solvent was removed b...

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Abstract

The invention discloses a pyrrolo[3,2-d] pyrimidine compound, and a preparation method and a purification method thereof. A condensed chemical structural formula of the pyrrolo[3,2-d] pyrimidine compound is shown in the description, wherein R1 represents halogen or methyl; R2 represents hydrogen, aryl, substituted aryl or alkyl. The prepared pyrrolo[3,2-d] pyrimidine compound is novel in structure; many active natural products and medicaments contain similar indole structures, so that the compound has high application value for the total synthesis of natural products and new medicament discovery, and has a broad application prospect.

Description

technical field [0001] The invention relates to a pyrrolopyrimidine compound material, in particular to a pyrrolo[3,2-d]pyrimidine compound, a preparation method and a purification method thereof, and belongs to the technical field of organic synthesis. Background technique [0002] Indole compounds are a class of important skeleton structure compounds with special medicinal compounds, which widely exist in natural products and drugs, and have good biological activities. Indole secondary metabolites are widely present in many natural products, such as cruciferous vegetables, a large number of marine organisms, and actinomycete species. At present, drugs containing indole structures such as sunitinib, vinblastine, and vincristine have been marketed and put into clinical use. Due to their wide range of biological activities, indole compounds have attracted much attention in the research of anticancer drugs. In the prior art, there are few reports on pyrrolo[3,2-d]pyrimidines...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D239/48
CPCC07D487/04C07D239/48
Inventor 张士磊谢瑞胡延维陈韶华
Owner SUZHOU UNIV
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