Polysubstituted purine derivatives as well as preparation method and application thereof
A technology of purines and derivatives, applied in the medical field, can solve unseen problems and achieve the effect of reducing by-products, complete reaction, and high antiviral activity
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Embodiment 1
[0040] Synthesis of [2-[(2-nitro-4-hydroxy-5-yl)pyrimidine]-4-pyridine]purin-8-yl-carboxylic acid (D).
[0041] Structural formula:
[0042] .
[0043] (2-Chloro-6-pyridine)purin-8-ylcarboxylic acid (B) (5g, 1.8mol) and (2-nitro-4-hydroxy)pyrimidin-5-yl-boronic acid dimethyl ester (C) ( 5.8g, 2.3mol) into the reaction vessel, in the presence of the organic solvent dichloromethane (50ml) and sodium carbonate (0.8g), add the catalyst 1,1'-bis(diphenylphosphino)ferrocene chloride Palladium (0.32g), heated to 85°C in a water bath and kept stirring, TLC detected that the reaction was complete, generating [2-[(2-nitro-4-hydroxy-5-yl)pyrimidine]-4-pyridine]purine-8- Dimethyl-formic acid (D) (9.69g, 2.4mol).
[0044] Synthesis of [2-[(2-nitro-4-hydroxy-5-yl)pyrimidine]-4-pyridine]purin-8-yl-formyl chloride (E).
[0045] Structural formula:
[0046] .
[0047] The [2-[(2-nitro-4-hydroxy-5-yl)pyrimidine]-4-pyridine]purin-8-yl-formic acid (D) (9.69g, 2.4mol) generated above was...
Embodiment 2-4
[0054] The catalyst in Example 1 was changed, and other operations were unchanged, and the operation steps of Example 1 were repeated to obtain Examples 2-4, and the results are shown in the following table.
[0055]
[0056] In conjunction with embodiment 1 and embodiment 2~4, catalyzer has important influence to the synthesis of the present invention, uses 1,1'-two (diphenylphosphino) ferrocene palladium chloride to make catalyst and has good catalytic effect, does not Using a catalyst or using palladium as a catalyst or using 1,1'-bis(di-phenylphosphino)ferrocene as a catalyst, the final yield is 10.58% or 60.12% or 48.77%, which seriously affects [2-[( Yield of 2-nitro-4-hydroxy-5-yl)pyrimidin]-4-pyridine]purin-8-yl-formic acid-(2-chloro-4-methyl)phenyl ester (A).
Embodiment 5
[0058] The alkali in Example 1 was removed, and other operations were unchanged, and the operation steps of Example 1 were repeated to obtain Example 5. The results are shown in the table below.
[0059]
[0060] In combination with Example 1 and Example 5, in the absence of alkali, the final [2-[(2-nitro-4-hydroxy-5-yl)pyrimidine]-4-pyridine]purin-8-yl-formic acid-( The yield of 2-chloro-4-methyl)phenyl ester (A) is greatly reduced, so the base plays an important role in the reaction of the present invention.
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