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Preparing method and intermediates of pyrrolo[3,2-d]pyrimidine compounds

A compound, selected technology, applied in the direction of organic chemistry, resistance to vector-borne diseases, etc., can solve problems such as side effects

Inactive Publication Date: 2017-08-15
CHIA TAI TIANQING PHARMA GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Interferon α is one of the main drugs for the treatment of chronic hepatitis B or C, while TNF-α is a pro-inflammatory cytokine, excessive secretion may lead to serious side effects

Method used

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  • Preparing method and intermediates of pyrrolo[3,2-d]pyrimidine compounds
  • Preparing method and intermediates of pyrrolo[3,2-d]pyrimidine compounds
  • Preparing method and intermediates of pyrrolo[3,2-d]pyrimidine compounds

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preparation example Construction

[0008] As a preferred embodiment, the preparation method of the compound of formula I uses the compound of formula II as a raw material, comprising the following steps:

[0009] (a) the compound of formula II and the compound of formula III react to obtain the compound of formula IV in the presence of a base,

[0010]

[0011] (b) the compound of formula IV and the compound of formula V react to obtain the compound of formula VI in the presence of a reducing agent,

[0012]

[0013] (c) the compound of formula VI obtains the compound of formula I through dehydroxylation,

[0014]

[0015] Among them, R 1 and R 2 independently selected from C 1 ~C 4 the alkyl group, or, R 1 , R 2 Together with the connected N atom, a 4-8 membered heterocycloalkyl group is formed, and the heterocycloalkyl group is optionally substituted by one or more substituents independently selected from hydroxyl, halogen, C 1 ~C 4 Alkyl or C 1 ~C 4 of alkoxy.

[0016] As another preferre...

Embodiment approach

[0024] As an embodiment of the present invention, the reducing agent is selected from BH 3 , NaBH 4 , NaBH 3 CN or NaBH(AcO) 3 , preferably NaBH(AcO) 3 .

[0025] As an embodiment of the present invention, the molar ratio of the compound of formula IV to the reducing agent is selected from 1.0:1.0-3.0, preferably 1.0:1.2-2.0, more preferably 1.0:1.5.

[0026] As an embodiment of the present invention, step (b) is carried out in the presence of an acid selected from hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, formic acid, acetic acid, propionic acid, citric acid, fumaric acid, apple acid, succinic acid, salicylic acid, maleic acid or trifluoroacetic acid, preferably acetic acid.

[0027] As an embodiment of the present invention, in step (b), the molar ratio of the compound of formula IV to the acid is selected from 1.0:1.0-3.0, preferably 1.0:1.2-2.0, more preferably 1.0:1.5.

[0028] As a preferred embodiment of the present invention, the dehydr...

preparation Embodiment 1

[0051] Preparation Examples of Compounds of Formula I is the preparation of the formula I compound of 1)

[0052] 1-1. Preparation of 4-((4-amino-2-butoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-hydroxymethyl)benzaldehyde (compound of formula IV)

[0053]

[0054] Put terephthalaldehyde (790.64mg, 5.82mmol) and isopropanol (10mL) into a three-necked flask, and add 2-butoxy-5H-pyrrolo[3,2-d]pyrimidin-4-amine under stirring (1.00g, 4.85mmol), cooled to 0°C, then continued to stir for 10min, added purified water (10mL) and potassium carbonate (804.17mg, 5.82mmol), reacted at 25°C for 16hr, monitored by LCMS until the reaction of the raw materials was complete, after the reaction was complete , a solid precipitated out. Filtration, the resulting solid was slurried with 20 mL of purified water, then 30 mL (ethyl acetate / n-heptane=1 / 20), filtered, and dried to obtain the title compound as a yellow solid (1.50 g, 4.41 mmol, yield: 90.9%) .

[0055] 1 H NMR (400MHz, methanol-d 4 )δ9...

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Abstract

The invention relates to the field of pharmaceutical chemistry, and particularly relates to a preparing method and intermediates of pyrrolo[3,2-d]pyrimidine compounds (compounds of a formula I). The method includes a step of subjecting compounds of a formula VI to dehydroxylation to obtain the compounds of the formula I. As a preferential implementing mode, the method includes reacting a compound of a formula II that is adopted as a raw material and a compound of a formula III under the existence of an alkali to obtain a compound of a formula IV, reacting the compound of the formula IV and a compound of a formula V under the existence of a reductant to obtain a compound of a formula VI, and subjecting the compound of the formula VI to dehydroxylation to obtain the corresponding compound of the formula I; or reacting the compound of the formula II and a compound of a formula III' under the existence of an alkali to obtain the compound of the formula VI and subjecting the compound of the formula VI to dehydroxylation to obtain the corresponding compound of the formula I. Reaction conditions of the method are mild. Use of expensive and highly dangerous agents is avoided. The method is particularly suitable for industrial production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular, the invention relates to a preparation method of pyrrolo[3,2-d]pyrimidine compounds and intermediates thereof. Background technique [0002] Toll-like receptors are expressed on a variety of immune cells. Toll-like receptors recognize highly conserved structural motifs: pathogen-associated microbial patterns (PAMPs) expressed by microbial pathogens or damage-associated molecular patterns (DAMPs) released by necrotic cells. Stimulation of Toll-like receptors via the corresponding pathogen-associated microbial patterns (PAMPs) or damage-associated molecular patterns (DAMPs) initiates signaling cascades leading to activation of transcription factors such as AP-1, NF-κB and interferon regulators (impulse response functions) activation. This results in a variety of cellular responses, including the production of interferons, proinflammatory cytokines, and effector cytokines, resulti...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04C07D487/00
Inventor 丁照中孙飞胡迎虎周义龙赵锐杨玲
Owner CHIA TAI TIANQING PHARMA GRP CO LTD
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