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2,4-carbon-oxo-bridged pyrimidine cyclized product and its preparation method and application

A technology of base pyrimidine and cyclized compound, which is applied in the field of 2,4-carbon-oxygen bridge pyrimidine cyclized compound and its preparation, and can solve the problems that have not been reported in the literature.

Active Publication Date: 2016-06-29
江苏笃诚医药科技股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, a class of cyclic ether uracil derivatives of the present invention, i.e. 2,4-carbon-oxygen bridge pyrimidine cyclized compound and its hydrogen halide salt (I) have not been reported in the literature

Method used

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  • 2,4-carbon-oxo-bridged pyrimidine cyclized product and its preparation method and application
  • 2,4-carbon-oxo-bridged pyrimidine cyclized product and its preparation method and application
  • 2,4-carbon-oxo-bridged pyrimidine cyclized product and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 19

[0024] Preparation of Example 19-Methyl-2,5-dioxa-7,10-diazabicyclo[4.3.1]dec-1(10),6,8-triene

[0025] Suspend 10.0g (79mmol) of 5-methyluracil in 102g hexamethyldisilazane amine (635mmol), add 0.1g ammonium sulfate and heat to reflux, react overnight, until the reaction solution is clear, evaporate under reduced pressure to recover excess Hexamethyldisilazane; add 80mL of dried 1,2-dichloroethane to the residue, dissolve and cool to 5°C, slowly add 7g of SnCl 4 and 10mL of 1,2-dichloroethane, after dropping, the reaction solution was heated to a slight reflux state until the completion of the reaction was detected by TLC. Cool the reaction solution to 5-10°C, add saturated NaHCO under stirring 3 Aqueous solution, to neutral, precipitated, precipitated as Sn hydroxide, filtered, concentrated the filtrate under reduced pressure, removed the reaction solvent and half the volume of water, cooled and stood still, precipitated the product solid, filtered, and then purified by wat...

Embodiment 2

[0035] On the basis of embodiment 1, apply above-mentioned catalyst SnCl 4 , raw material ratio, reaction conditions and operation methods, change the substituent on the uracil ring and 1, n-dihaloalkane (n=0,1,2), the resulting 2,4-carbon-oxygen bridging pyrimidine ring The yields of the compounds are shown in Table 1 below.

[0036] Table 1 The yield of 2,4-carbon-oxo-bridged pyrimidine cyclizations corresponding to different substituents

[0037]

[0038]

Embodiment 3

[0040] On the basis of Example 1, apply the above-mentioned raw material ratio, reaction conditions and operation method, change catalyst ZnCl 2 , substituents on the uracil ring and 1, n-dihaloalkane (n=0,1,2), the yield of the obtained 2,4-carbon-oxygen bridging pyrimidine cyclization is shown in Table 2.

[0041] Table 2 The yields of 2,4-carbon-oxygen-bridged pyrimidine cyclizations corresponding to different substituents and catalysts

[0042]

[0043]

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Abstract

The invention discloses a 2,4-carbon-oxygen bridge pyrimidine cyclic compound, and a preparation method and an application thereof. The compound belongs to cyclic ether uracil derivatives with a brand new structure. The structure of the derivatives is represented by general formula (I) shown in the specification. The compound can be used as a raw material of nanometer molecular devices and nanometer self-assembled parts.

Description

technical field [0001] The invention relates to a raw material for nanomolecular devices and nanometer self-assembled components and a preparation method thereof, in particular to a class of novel 2,4-carbon-oxygen bridge pyrimidine cyclizations and a preparation method and application thereof. Background technique [0002] The 2-position and 4-position of pyrimidine alone or simultaneously acyclic etherification products are often used as raw materials for nanomolecular devices and nanometer self-assembly components (DrexlerKE, Natosystems-molecularmachinery, manufacturingandcomputation, WileyInterscience: NewYork, 1992; AmabilinoDB, WilliamsDJ, etal.JAmChemSoc, 1995, 117(45): 11142~11170), and most of these ether compounds are made of 2,4-dihalopyrimidine, reacted with alcohols under the action of strong base (such as NaH, etc.) Obtained, or also use uracil as raw material and hydrocarbon sulfonate under catalyst action. [0003] So far, a class of cyclic ether uracil der...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/08
CPCC07D491/08
Inventor 姚其正李民权王笃政王玉祥姚世宁李亚琳
Owner 江苏笃诚医药科技股份有限公司