52217-39-7

Upstream product

• 77746-95-3 3-Methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 5-oxide 
• 58668-41-0 N'-(4-formyl-5-methyl-2-phenyl-2H-pyrazol-3-yl)-N,N-dimethyl-formamidine 
• 1131-18-6 1-Phenyl-3-methyl-5-aminopyrazole 
• 2590-03-6 N-(3-methyl-1-phenyl-1H-pyrazol-5-yl)acetamide 
• 64664-15-9 N-(3-methyl-1-phenyl-1H-pyrazol-5-yl)benzamide 
• 77287-34-4 formamide 
• 52217-35-3 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 100-63-0 phenylhydrazine 
• 87412-84-8 4-amino-3-methyl-1-phenylpyrazolo<3,4-d>pyrimidine 
• 100-66-3 methoxybenzene 
• 53106-26-6 N-(5-methyl-2-phenyl-2H-pyrazol-3-yl)-formamide 

Relevant academic research and scientific papers

One-flask synthesis of pyrazolo[3,4-d]pyrimidines from 5-aminopyrazoles and mechanistic study

A novel one-flask synthetic method was developed in which 5-aminopyrazoles were reacted with N,N-substituted amides in the presence of PBr3. Hexamethyldisilazane was then added to perform heterocyclization to produce the corresponding pyrazolo[

Evaluation of electrophilic heteroaromatic substitution: Synthesis of heteroaromatic-fused pyrimidine derivatives via sequential three-component heterocyclization

A new sequential three-component heterocyclization was developed by reacting aromatic and heterocyclic substrates, including aminobenzenes, 1-aminonaphthalene, 2-aminopyrazines, 5-aminopyrazoles, 3-aminopyridine, 5-aminopyrimidine, 5-aminoquinoline, and 8

One-pot synthesis and antiproliferative evaluation of pyrazolo[3,4-d] pyrimidine derivatives

An efficient one-pot methodology for the synthesis of pyrazolo[3,4-d] pyrimidines was developed by using 5-aminopyrazoles with formamide in presence of PBr3 as the coupling agent. Among the examples presented in this work, compounds 41 and 54-5

Aryl Coupling Reactions of Pyrazolopyrimidin-4-yl Radicals

4-Arylpyrazolopyrimidines (4) were the subjects of a synthetic investigation in order to evaluate their biological activity.Attempts to prepare 4 from 4-aminopyrazolopyrimidines (5) via classical Gomberg-Bachmann-Hey aryl coupling conditions failed.Conversion of 5 to 4 was accomplished by diazotiazation of 5 using alkyl nitrites with an acid catalyst in aromatic solvents.Isomer distribution of the aryl-coupled products 4 was that predicted for a radical intermediate (ortho > meta ca. para); isomer structures were assigned by a detailed 1H NMR analysis.Unusual fragmentation products 17 and 18 were isolated during the course of investigations.These oxadiazoles probably arise from collapse of intermediate pyrazolopyrimidin-4-yl radicals 15.

VILSMEIER-HAACK REACTION OF 5-AMINO- AND 5-ACYLAMINO-PYRAZOLES

The Vilsmeier-Haack reaction of 5-aminopyrazole derivatives 1 was investigated in view of contradictory literature reports.Structure 2 of the products was proved both chemically and spectroscopically.The mechanism of the reaction was postulated on the basis of isolated intermediates 7 and 8. 5-Acylaminopyrazoles 9, 10 and 11 were found to give also 2 (and 7) under the Vilsmeier conditions by an acyl splitting reaction, proceeding probably via diacylamino derivatives 12.Compounds 2 provided a simple route to pyrazolopyrimidine derivatives 13 and 14 as well as to azomethine compounds 15-18.