1h-Pyrazolo[3,4-d]pyrimidine

Base Information

• Chemical Name: 1h-Pyrazolo[3,4-d]pyrimidine
• CAS No.: 271-80-7
• Molecular Formula: C5H4N4
• Molecular Weight: 120.114
• Hs Code.: 2933990090
• NSC Number: 82206
• DSSTox Substance ID: DTXSID60181566
• Nikkaji Number: J1.517.897C
• Wikidata: Q83052192
• Mol file: 271-80-7.mol

Synonyms:A-420983;pyrazolo(3,4-d)pyrimidine

Chemical Property of 1h-Pyrazolo[3,4-d]pyrimidine

Chemical Property:

• Vapor Pressure: 0.000966mmHg at 25°C
• Melting Point: 213-214 °C
• Refractive Index: 1.737
• Boiling Point: 312.5°C at 760 mmHg
• PKA: 11.53±0.20(Predicted)
• Flash Point: 158.7°C
• PSA: 54.46000
• Density: 1.472g/cm³
• LogP: 0.35290
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 120.043596145
• Heavy Atom Count: 9
• Complexity: 105

Purity/Quality:

97% ^*data from raw suppliers

1H-Pyrazolo[3,4-d]pyrimidine 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C2C=NNC2=NC=N1

Technology Process of 1h-Pyrazolo[3,4-d]pyrimidine

There total 3 articles about 1h-Pyrazolo[3,4-d]pyrimidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-chloro-1H-pyrazolo[3,4-d]pyrimidine (5399-92-8) → 1H-pyrazolo[3,4-d]pyrimidine (271-80-7,35760-86-2)

Guidance literature:

With ammonium hydroxide; palladium on activated charcoal; Hydrogenation;

DOI:10.1021/ja01585a023

Reference yield:

Allopurinol (315-30-0) → 1H-pyrazolo[3,4-d]pyrimidine (271-80-7,35760-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-dimethyl-aniline; POCl₃

2: palladium/charcoal; aqueous NH₃ / Hydrogenation

With ammonium hydroxide; palladium on activated charcoal; N,N-dimethyl-aniline; trichlorophosphate;

DOI:10.1021/ja01585a023

Reference yield:

→ 1H-pyrazolo[3,4-d]pyrimidine (271-80-7,35760-86-2)

Guidance literature:

(XV),Raney-Nickel/EtOH;

upstream raw materials:

4-chloro-1H-pyrazolo[3,4-d]pyrimidine

Allopurinol

Downstream raw materials:

1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidine

2-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-2H-pyrazolo[3,4-d]pyrimidine

1H-pyrazolo<3,4-d>pyrimidin-4(5H)-one

1-(2-fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carbonitrile

Refernces

FREE-RADICAL HYDROXYMETHYLATION OF BENZIMIDAZOLE

10.1007/BF00506621

The research investigates the free-radical hydroxymethylation of benzimidazole derivatives and the condensation of 3,4-dicyano-5-aminopyrazole with ethyl orthoformate. In the hydroxymethylation study, benzimidazole derivatives such as 1-methylbenzimidazole and 1-phenylbenzimidazole were subjected to free-radical hydroxymethylation using ammonium persulfate in methanol and sulfuric acid, with silver ions as a catalyst to enhance yields. The study found that benzimidazole displayed lower activity than quinoline in the addition of the hydroxymethyl radical, and the yields of hydroxymethylation products were influenced by the ability of intermediate benzimidazolium cation radicals to undergo oxidation. In the condensation study, 3,4-dicyano-5-aminopyrazole was reacted with ethyl orthoformate under different conditions to produce compounds like N-ethyl-3,4-dicyano-5-ethoxymethyleneaminopyrazole and 3,4-dicyano-5-ethoxymethyleneaminopyrazole. The formation of these products and their subsequent conversion to pyrazolo[3,4-d]pyrimidines using a methanol solution of ammonia were also explored.