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Method for synthesizing 2/6-iodo-purine derivative through visible light induced hydrazine removal-iodination reaction

A technology of derivatives, iodopurine, is applied in the field of visible light-induced dehydrazine-iodination reaction to synthesize 2/6-iodopurine derivatives, can solve problems such as narrow application range, and achieve wide applicability, simple operation and safety factor high effect

Active Publication Date: 2022-07-22
XINXIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method not only requires low temperature, but also can only obtain 6-iodopurine, so the scope of application is narrow

Method used

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  • Method for synthesizing 2/6-iodo-purine derivative through visible light induced hydrazine removal-iodination reaction
  • Method for synthesizing 2/6-iodo-purine derivative through visible light induced hydrazine removal-iodination reaction
  • Method for synthesizing 2/6-iodo-purine derivative through visible light induced hydrazine removal-iodination reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] In a transparent glass reaction flask, add (0.24g, 1mmol), diiodomethane (0.088mL, 1.1mmol) and eosin Y (0.0143g, 0.02mmol) were added to acetonitrile (2mL), turned on 5W visible light, stirred, irradiated at room temperature for 4h, TLC showed The raw materials reacted completely, the reaction solution was concentrated under reduced pressure, and separated by column chromatography to obtain 0.299g, yield 89%.

[0025] 1 H NMR (400MHz, DMSO-d 6 )δ8.78(s,1H),8.13(s,1H),7.37-7.31(m,5H),5.47(s,2H); 13 C NMR (100MHz, DMSO-d 6 )δ152.1,151.8,151.0,134.5,131.5,129.2,128.8,127.9,68.7,47.8.

Embodiment 2

[0027] by As the raw material, other reaction conditions were changed, and the reaction results were shown in the following table:

[0028]

Embodiment 3

[0030] In a transparent glass reaction flask, add (0.297g, 1mmol), diiodomethane (0.081mL, 1mmol) and eosin Y (0.0143g, 0.02mmol) were added to acetonitrile (5mL), turned on 5W visible light, stirred, irradiated at room temperature for 6h, TLC showed the raw materials The reaction was complete, the reaction solution was concentrated under reduced pressure, and recrystallized from ethanol to obtain 0.294g, yield 75%.

[0031] 1 H NMR (400MHz, DMSO-d 6 )δ8.15(s,1H),7.37(brs,2H,NH 2 ),5.89(d,J=6.4Hz,1H),5.47(t,J=6.4Hz,2H),5.23(d,J=4.8Hz,1H),4.64-4.60(m,1H),4.17-4.14 (m, 1H), 3.99-3.96 (m, 1H), 3.70-3.66 (m, 1H), 3.59-3.53 (m, 1H); 13 C NMR (100MHz, DMSO-d 6 )δ152.5,149.4,140.4,118.3,84.1,83.6,75.7,75.0,68.2,60.9.

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Abstract

The invention discloses a method for synthesizing a 2 / 6-iodo-purine derivative through visible light induced hydrazine removal-iodination reaction, and belongs to the technical field of medicine synthesis. In an organic solvent, a 2-hydrazino purine derivative or a 6-hydrazino purine derivative and diiodomethane are used as raw materials and react at room temperature under the irradiation of visible light in the presence of a photocatalyst to obtain the 2-iodopurine derivative or the 6-iodopurine derivative. According to the method for converting hydrazino into iodo, heating is not needed, only visible light irradiation is adopted, use of an additional oxidizing agent is avoided, the cost is low, operation is easy, and the safety coefficient is high.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, in particular to a method for synthesizing 2 / 6-iodopurine derivatives by visible light-induced dehydration-iodination reaction. Background technique [0002] Iodopurine is an important intermediate in the synthesis of nucleoside drugs, which is divided into 6-iodo, 8-iodo and 2-iodopurine and purine nucleosides. Through metal coupling reactions such as Suzuki and Sonogashira, alkenyl Hydrophobic groups such as alkynyl groups, alkynyl groups, and fused-ring aryl groups are easily connected to purines to obtain drugs with higher physiological activity and better curative effect, or further convert them into fluorescent molecules that can be used as DNA probes. It has a wide range of applications in therapy, biochemistry and chemical synthesis. At present, the synthesis of iodopurine derivatives is usually divided into four types of reaction systems: [0003] 1. Utilize amino group to repla...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/40
CPCC07D473/40
Inventor 孙莉萍陈磊山夏然
Owner XINXIANG UNIV
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