112581-74-5

Usage

Uses

Used in Pharmaceutical Industry:
2,5,7-Trimethylpyrazolo[1,5-a]pyrimidine is used as a therapeutic agent for the treatment of various neurological disorders. Its antagonistic effect on the adenosine A1 receptor and agonistic effect on the A2A receptor make it a promising candidate for managing neurodegenerative diseases, Parkinson's disease, and Alzheimer's disease.
Used in Cancer Research:
In the field of cancer research, 2,5,7-Trimethylpyrazolo[1,5-a]pyrimidine is utilized as an inhibitor of cancer cell growth and proliferation. Its potential to target and suppress the development of cancer cells has positioned it as a valuable compound in the search for novel cancer treatments.

InChI:InChI=1/C9H11N3/c1-6-4-8(3)12-9(10-6)5-7(2)11-12/h4-5H,1-3H3

Upstream product

• 31230-17-8 3-amino-5-methylpyrazole 
• 123-54-6 acetylacetone 
• 431-03-8 dimethylglyoxal 

Relevant academic research and scientific papers

Pyrazolopyrimidines based on 5-aminopyrazoles unsubstituted at the position 1

By condensation of various symmetric β-diketones with a series of 5-aminopyrazoles that are unsubstituted at the position 1, we have obtained a series of pyrazolo[1,5-a]pyrimidines that are of interest as physiologically active compounds. Hexafluoroacetylacetone reacts in another direction, forming pyrazolo[4,5-b]pyridine.

Reactivity of electrogenerated thiocyanogen in the thiocyanation of pyrazolo[1,5-a]pyrimidines

Selective thiocyanation (yield 70–90%) at the 3-position of pyrazolo[1,5-a]pyrimidines was performed with thiocyanogen electrochemically generated in situ from NH4SCN in MeCN on a Pt anode. For substrates with higher oxidation potential addition of Lewis acids was necessary.

Convenient synthesis of substituted 3-alkenylpyrazolo[1,5-a]pyrimidines via Heck cross-coupling reaction

3-Iodopyrazolo[1,5-a]pyrimidines 3 were easily obtained by direct iodination of pyrazolo[1,5-a]pyrimidines 2 with NIS and could be transformed into a series of new substituted 3-alkenyl-pyrazolo[1,5-a]pyrimidines 5 by Heck cross-coupling.

Chemical and Electrochemical Reduction of some Pyrazolopyrimidines

Various pyrazolopyrimidines 1 are prepared by two different ways.Their chemical reduction by sodium borohydride leads generally to 4,5,6,7-tetrahydro compounds 3, while lithium aluminum hydride yields 4,7-dihydro derivatives 2 at room temperature, and 3 in refluxing tetrahydrofuran.A complex mixture of oxidizable hydrodimers is obtained by electrochemical reduction.An electroreduction at a more negative potential also gives 4,7-dihydro compounds 2.A new 4,5-dihydropyrazolopyrimidine has been obtained by condensation of 5-amino-3-methyl-1H-pyrazole with acetophenone.