6288-86-4

Basic information

• Product Name: 1H-Pyrazolo[3,4-d]pyrimidine, 1-methyl- (6CI,8CI,9CI)
• Synonyms: 1H-Pyrazolo[3,4-d]pyrimidine, 1-methyl- (6CI,8CI,9CI);1-Methyl-1H-pyrazolo[3,4-d]pyrimidine
• CAS NO: 6288-86-4
• Molecular Formula: C₆H₆N₄
• Molecular Weight: 134.14
• Product Categories: PYRIMIDINE
• Mol File: 6288-86-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 255.7°C at 760 mmHg
• Flash Point: 108.4°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 0.0257mmHg at 25°C
• Refractive Index: 1.722
• CAS DataBase Reference: 1H-Pyrazolo[3,4-d]pyrimidine, 1-methyl- (6CI,8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazolo[3,4-d]pyrimidine, 1-methyl- (6CI,8CI,9CI)(6288-86-4)
• EPA Substance Registry System: 1H-Pyrazolo[3,4-d]pyrimidine, 1-methyl- (6CI,8CI,9CI)(6288-86-4)

Safety Data

• Hazardous Substances Data: 6288-86-4(Hazardous Substances Data)

Usage

General Description

1H-Pyrazolo[3,4-d]pyrimidine, 1-methyl- (6CI,8CI,9CI) is a scientific name for a specific chemical compound. 1H-Pyrazolo[3,4-d]pyrimidine, 1-methyl- (6CI,8CI,9CI) is characterized by the presence of a pyrazolo [3,4-d] pyrimidine nucleus, which is a heterocyclic compound, indicating that it contains atoms of at least two different elements in its rings. This yet falls into the larger group of pyrimidines, which themselves are aromatic heterocyclic organic compounds similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring. As a 1-methyl derivative, the compound also has one methyl group (-CH3) attached to it. The chemical identifiers (6CI,8CI,9CI) are a type of registry number used for precise identification in chemical databases.

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

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.