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New compound, preparation method and application thereof

A compound and reaction technology, applied in the field of the new compound 4,6-dichloropyrimidine-5-acetaldehyde-O-methyl oxime, can solve the problems of difficult completion of the reaction, difficult post-processing, high price, etc., and achieve simple operation. , the raw materials are easily available, and the product purity is good.

Inactive Publication Date: 2019-05-07
宁夏中星显示材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the above methods, osmium tetroxide and potassium osmate are expensive, highly toxic, and difficult to post-process, and it is difficult to complete the reaction of ozone as an oxidant, and the risk is high

Method used

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  • New compound, preparation method and application thereof
  • New compound, preparation method and application thereof
  • New compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] (1), the synthesis of 2-chloroacetaldehyde-O-methyl oxime (c) (below ①, ②, ③ three examples)

[0036] ①Put 217.1g (2.6mol) of methoxylamine hydrochloride into a 2L three-necked flask, add 350mL of water, stir and dissolve, then add dropwise 249.1g (2mol) of chloroacetaldehyde dimethyl acetal, and drop it in 30 minutes. Raise the temperature to 40°C and react for 20 hours. Sampling and detection showed that almost no raw materials remained, and the reaction was completed. Post-treatment: Cool the reaction solution below 30°C, add 300mL of dichloromethane, stir for 10 minutes to separate the liquid, extract the water layer with 150mL×2 dichloromethane, combine the organic layer, wash the organic layer with 200mL×2 water, separate the liquid, and discard the water layer. The organic layer was fully dried with 50 g of anhydrous sodium sulfate, filtered, and the filter cake was washed with 100 mL of dichloromethane. The filtrate was precipitated and then rectified to obtain...

Embodiment 2

[0051] Example 2 The nuclear magnetic resonance spectrum of 4,6-dichloropyrimidine-5-acetaldehyde-O-methyloxime

[0052] ①Chemical structural formula and hydrogen atom number

[0053]

[0054] ② Measuring instruments, conditions and testing units

[0055] Instrument model: Bruker AVANCE III HD 400MHz

[0056] Test conditions: solvent: deuterated chloroform; internal standard: tetramethylsilane (TMS)

[0057] Test unit: Hebei Sundia Pharmaceutical Technology Co., Ltd.

[0058] ③ Results: See Table 1 for H NMR spectrum data

[0059] Table 1 1 H-NMR data and assignment

[0060]

Embodiment 3

[0061] Example 3 Detection of impurities and purity of 4,6-dichloropyrimidine-5-acetaldehyde-O-methyloxime

[0062] ① Testing instruments and testing conditions

[0063] Detection instrument: Agilent 1260

[0064] Chromatographic conditions and system: mobile phase: methanol: 0.1% acetic acid water = 70:30; detection wavelength: 254nm; flow rate: 0.5mL / min.

[0065] ②Sample configuration

[0066] Weigh 0.0050g sample, dissolve in 7mL mobile phase, and ultrasonically dissolve.

[0067] ③Test results

[0068] Table 2 The data of each substance in the HPLC spectrum

[0069]

[0070] The compound is cis-trans isomers, of which the trans-form accounts for about 47.2%, and the cis-form accounts for 52.7%. Numbers 1 and 2 are the impurity information of the compound; 3 and 4 are products.

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Abstract

Belonging to the technical field of organic chemistry, the invention provides a new compound, a preparation method and application thereof. The compound is named 4, 6-dichloropyrimidine-5-acetaldehyde-O-methyl oxime, has a molecular formula of C7H7Cl2N3O and a relative molecular mass of 220.06, and is a light yellow solid in appearance. The preparation method of the new compound has the advantagesof easily available raw materials, simple operation, good product purity, high yield, etc., and is easy for industrial production. The new compound 4, 6-dichloropyrimidine-5-acetaldehyde-O-methyl oxime can be subjected to one-step reaction to obtain 4, 6-dichloropyrimidine-5-acetaldehyde. The new compound can be applied as an important intermediate in pharmaceutical field.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and relates to a new compound 4,6-dichloropyrimidine-5-acetaldehyde-O-methyloxime, a preparation method and a pharmaceutical application of the new compound. The chemical name of the new compound prepared is 4,6-dichloropyrimidine-5-acetaldehyde-O-methyloxime, and the molecular formula is C 7 h 7 Cl 2 N 3 O, the relative molecular mass is 220.06, the appearance is a light yellow solid, and its nuclear magnetic resonance spectrum is as follows figure 1 shown. 4,6-dichloropyrimidine-5-acetaldehyde-O-methyloxime is a newly designed and synthesized compound, and there is no literature report at home and abroad. Background technique [0002] 4-Chloro-7H-pyrrole[2,3-d]pyrimidine can be used to prepare drugs such as "Tofacitinib", "ruxolitinib", "baricitinib", and is an important drug intermediate . At present, an important construction method of 4-chloro-7H-pyrrole[2,3-d]pyrimidine is ...

Claims

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Application Information

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IPC IPC(8): C07D239/30C07D487/04
Inventor 岳刚王志强陈少华禹凯王利民关登仕
Owner 宁夏中星显示材料有限公司