6288-86-4

Usage

Uses

1H-Pyrazolo[3,4-d]pyrimidine, 1-methyl(6CI,8CI,9CI) is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its heterocyclic structure and the presence of a methyl group make it a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Pharmaceutical Industry:
1H-Pyrazolo[3,4-d]pyrimidine, 1-methyl(6CI,8CI,9CI) is used as a key component in the synthesis of novel drug candidates for the treatment of various diseases. Its unique chemical structure allows for the exploration of new chemical entities with improved pharmacological properties, such as increased potency, selectivity, and reduced side effects.

InChI:InChI=1/C6H6N4/c1-10-6-5(3-9-10)2-7-4-8-6/h2-4H,1H3

Upstream product

• 23000-43-3 4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine 
• 77287-34-4 formamide 
• 1192-21-8 5-Amino-1-methylpyrazole 
• 271-80-7 1H-pyrazolo[3,4-d]pyrimidine 
• 74-88-4 methyl iodide 

Downstream Products

• 116943-93-2 5-Benzoyl-1-methyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-4-carbonitrile 

Relevant academic research and scientific papers

Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4- d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds

Alkylation of 4-methoxy-1H-pyrazolo[3,4-d]pyrimidine (1b) with iodomethane in THF using NaHMDS as base selectively provided N2-methyl product 4-methoxy-2-methyl-2H-pyrazolo[3,4-d]pyrimidine (3b) in an 8/1 ratio over N1-methyl product (2b). Interestingly, conducting the reaction in DMSO reversed selectivity to provide a 4/1 ratio of N1/N2 methylated products. Crystal structures of product 3b with N1 and N7 coordinated to sodium indicated a potential role for the latter reinforcing the N2-selectivity. Limits of selectivity were tested with 26 heterocycles which revealed that N7 was a controlling element directing alkylations to favor N2 for pyrazolo- and N3 for imidazo- and triazolo-fused ring heterocycles when conducted in THF. Use of 1H-detected pulsed field gradient-stimulated echo (PFG-STE) NMR defined the molecular weights of ionic reactive complexes. This data and DFT charge distribution calculations suggest close ion pairs (CIPs) or tight ion pairs (TIPs) control alkylation selectivity in THF and solvent-separated ion pairs (SIPs) are the reactive species in DMSO.

Selective synthesis of pyrazolo[3,4-d]pyrimidine, N-(1H-pyrazol-5-yl) formamide, or N-(1H-pyrazol-5-yl)formamidine derivatives from N-1-substituted-5-aminopyrazoles with new Vilsmeier-type reagents

Various halomethyleniminium salts as novel Vilsmeier agents were synthesized from formamide or N-methylformamide with POCl3. Treatment of N-1-substituted-aminopyrazoles including N-1-phenyl-5-aminopyrazoles, N-1-(2-pyridinyl)-5-aminopyrazoles,