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Synthetic method for 5-bromo-imidazo[1, 2-A]pyrimidine-3-carboxylate and corresponding acid thereof

A synthesis method and imidazo technology, applied in the field of fine organic synthesis, can solve the problems of harsh reaction conditions, poor reaction selectivity and long reaction time of the synthesis route, and achieve the effects of high yield, moderate reaction time and easy process control.

Inactive Publication Date: 2015-11-18
HENAN VIOLET TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The reaction conditions of the above synthetic route are harsh, the reaction selectivity is poor, the reaction time is long, and the yield is also low

Method used

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  • Synthetic method for 5-bromo-imidazo[1, 2-A]pyrimidine-3-carboxylate and corresponding acid thereof
  • Synthetic method for 5-bromo-imidazo[1, 2-A]pyrimidine-3-carboxylate and corresponding acid thereof
  • Synthetic method for 5-bromo-imidazo[1, 2-A]pyrimidine-3-carboxylate and corresponding acid thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] This example provides a synthesis method of ethyl 5-bromoimidazo[1,2-A]pyrimidine-3-carboxylate, whose structural formula is as follows:

[0038]

[0039] Add N,N-dimethylformamide dimethyl acetal (10mL) and 2-amino-5-bromopyrimidine (3.46g, 20mmol) to a 50ml single-necked round-bottomed flask, heat to reflux and stir for 0.5 hours, TLC Indicating that the reaction is complete, the N,N-dimethyl-N'-2-(5-bromo-pyrimidinyl)-formamidine intermediate was obtained, and the excess N,N-dimethylformamide dimethyl condensation was removed by rotary evaporation. Aldehyde, add N,N-dimethylformamide (DMF, 15 mL), NaHCO 3 (2.5g, 30mmol) and ethyl bromoacetate (5g, 30mmol), heated to reflux for 2 hours, the reaction was completed, cooled to room temperature, added 60mL of water and 20mL of ethyl acetate for extraction, separated the organic phase, and used ethyl acetate for the aqueous phase Extract (3×20mL), combine the organic phases, wash with water (2×15mL), wash with 20mL sat...

Embodiment 2

[0045] This example provides a synthesis method of ethyl 5-bromoimidazo[1,2-A]pyrimidine-3-carboxylate, whose structural formula is as follows:

[0046]

[0047] Add N,N-dimethylformamide dimethyl acetal (50mL), 2-amino-5-bromopyrimidine (6.92g, 40mmol) and dichloromethane (30ml) in a 100ml single-necked round bottom flask, Stir the reaction at room temperature for 2h, TLC shows that the reaction is complete, and N,N-dimethyl-N'-2-(5-bromo-pyrimidinyl)-formamidine intermediate is obtained, and the excess N,N-dimethyl N, N-dimethylformamide (DMF, 25mL), NaHCO 3 (6.72g, 80mmol) and ethyl bromoacetate (10g, 60mmol), heated to reflux for 1 hour, the reaction was completed, cooled to room temperature, the solution was transferred to a 250mL round bottom flask, 80mL of water and 30mL of ethyl acetate were added for extraction, The organic phase was separated, the aqueous phase was extracted with ethyl acetate (3×30mL), the organic phases were combined, washed with water (2×20mL)...

Embodiment 3

[0053] This example provides a synthesis method of ethyl 5-bromoimidazo[1,2-A]pyrimidine-3-carboxylate, whose structural formula is as follows:

[0054]

[0055] In a 500ml single-necked round bottom flask, add N,N-dimethylformamide dimethyl acetal (150mL) and 2-amino-5-bromopyrimidine (69.6g, 400mmol). Stir the reaction at room temperature for 2h, TLC Indicating that the reaction is complete, the N,N-dimethyl-N'-2-(5-bromo-pyrimidinyl)-formamidine intermediate was obtained, and the excess N,N-dimethylformamide dimethyl condensation was removed by rotary evaporation. Aldehyde, add N,N-dimethylformamide (DMF, 250 mL), NaHCO 3 (50g, 595mmol) and ethyl bromoacetate (97g, 580mmol), heated to reflux for 1 hour, the reaction was completed, cooled to room temperature, added 500mL of water and 250mL of ethyl acetate for extraction, separated the organic phase, and extracted the aqueous phase with ethyl acetate (3×80mL), combined the organic phases, washed with water (2×50mL), wash...

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Abstract

The invention discloses a synthetic method for for 5-bromo-imidazo[1, 2-A]pyrimidine-3-carboxylate and corresponding acid thereof. The synthetic method comprises: taking a compound as shown in formula (1) as a raw material, and reacting the raw material with a compound as shown in formula (2) to generate a compound as shown in formula (3); and reacting the compound as shown in formula (3) with alpha ester of halogenated acid, and purifying to obtain the 5-bromo-imidazo[1, 2-a]pyrimidine-3-carboxylate; and hydrolyzing and acidifying the 5-bromo-imidazo[1, 2-a]pyrimidine-3-carboxylate to obtain 5-bromo-imidazo[1, 2-a]pyrimidine-3-carboxylic acid. The synthetic method disclosed by the invention is short in synthesis route and high in yield, and raw materials are easily available.

Description

technical field [0001] The invention relates to the technical field of fine organic synthesis, in particular to a synthesis method of a class of 5-bromo-imidazo[1,2-A]pyrimidine-3-carboxylates and corresponding acids. Background technique [0002] Imidazo[1,2-A]pyrimidine carboxylic acids are a very important class of nitrogen-containing fused heterocyclic compounds, which have become a research hotspot for organic chemists and medicinal chemists because of their specific physiological activities. Many imidazo[1,2-A]pyrimidine carboxylic acid compounds have obvious inhibitory effects on many target enzymes, etc. They have antiviral, antibacterial, antimicrobial and anticytokinin activities, imidazo[1,2-A] Pyrimidine carboxylic acid compounds are also used in the research of drugs for gastric ulcer, diabetes and psychosis, especially in the treatment of tumors. For example, imidazo[1,2-A]pyrimidine carboxylic acid compounds are used in the research of type II diabetes (Journ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 王泰评李松田高航申海芳彭南玉侯金涛
Owner HENAN VIOLET TECH CO LTD
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