A method for synthesizing 5-bromo-1h-pyrazolo[3,4-b]pyrazine

By using 2-aminopyrazine as a raw material, a simple three-step reaction is adopted to synthesize 5-bromo-1H-pyrazolo[3,4-b]pyrazine, which solves the problems of complicated synthesis routes and low yield in the existing technology and realizes efficient and safe industrial production.

CN117903145BActive Publication Date: 2026-06-19BAIYIN KANG YUXIN BIOTECHNOLOGY CO LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
BAIYIN KANG YUXIN BIOTECHNOLOGY CO LTD
Filing Date
2024-01-15
Publication Date
2026-06-19

AI Technical Summary

Technical Problem

The existing synthetic route for 5-bromo-1H-pyrazolo[3,4-b]pyrazine is cumbersome, has low yield, and uses dangerous hydrazine as a raw material, making the synthesis inconvenient.

Method used

Using 2-aminopyrazine as a starting material, 5-bromo-1H-pyrazolo[3,4-b]pyrazine was synthesized through a three-step reaction. The method utilizes inexpensive and readily available bromine and iodine sources and trimethylsilyldiazomethane, avoiding the use of hazardous substances and employing a simple synthetic route.

Benefits of technology

It achieves high-yield and high-purity synthesis, simplifies operation steps, reduces costs, is suitable for industrial production, and eliminates the need for column chromatography separation, saving solvents.

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Abstract

This invention relates to a method for synthesizing 5-bromo-1H-pyrazolo[3,4-b]pyrazine, comprising the following steps: (S1) 2-aminopyrazine reacts with a bromine source to obtain 3,5-dibromo-2-aminopyrazine; (S2) 3,5-dibromo-2-aminopyrazine reacts with an iodine source and a diazotizing reagent to obtain 3,5-dibromo-2-iodopyrazine; (S3) 3,5-dibromo-2-iodopyrazine reacts with trimethylsilyldiazomethane under alkaline conditions and in the presence of a catalyst to obtain the product 5-bromo-1H-pyrazolo[3,4-b]pyrazine. This invention utilizes readily available and inexpensive 2-aminopyrazine as a starting material, and the synthetic route is completed in three steps. No hazardous or toxic controlled reagents are used in the synthesis, making it a highly industrially viable production method. The synthetic method of this invention achieves satisfactory yields and purity, and the entire synthesis process does not require column chromatography, saving solvents and being economical and environmentally friendly.
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