ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyrimidines Aminopyrimidine 4-Aminopyrazolo[3,4-d]pyrimidine

4-Aminopyrazolo[3,4-d]pyrimidine

Product Name4-Aminopyrazolo[3,4-d]pyrimidine
CAS2380-63-4
MFC5H5N5
MW135.13
EINECS219-174-6
MOL File2380-63-4.mol

Chemical Properties

Melting point	>325 °C(lit.)
Boiling point	238.81°C (rough estimate)
Density	1.3795 (rough estimate)
refractive index	1.7000 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	soluble in DMSO
form	powder to crystal
pka	12.12±0.20(Predicted)
color	White to Orange to Green
Water Solubility	Insoluble in water.
BRN	5824
InChI	1S/C5H5N5/c6-4-3-1-9-10-5(3)8-2-7-4/h1-2H,(H3,6,7,8,9,10)
InChIKey	LHCPRYRLDOSKHK-UHFFFAOYSA-N
SMILES	Nc1ncnc2[nH]ncc12
CAS DataBase Reference	2380-63-4(CAS DataBase Reference)
NIST Chemistry Reference	1H-pyrazolo[3,4-d]pyrimidin-4-amine(2380-63-4)
EPA Substance Registry System	1H-Pyrazolo[3,4-d]pyrimidin-4-amine (2380-63-4)

Safety Information

Hazard Codes	T
Risk Statements	25-36/37/38-23/24/25
Safety Statements	26-36/37/39-45-22-36
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS	UR0717000
TSCA	TSCA listed
HazardClass	6.1
PackingGroup	III
HS Code	29335990
Storage Class	6.1D - Non-combustible acute toxic Cat.3 toxic hazardous materials or hazardous materials causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
Toxicity	LD50 oral in rat: 141mg/kg

MSDS

Provider	Language
4-Aminopyrazolo[3,4-d]pyrimidine	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Description

4-aminopyrazolo[3,4-d]pyrimidine (4-APP), the isomer of adenine with the five-membered ring in the pyrazole configuration, is by far the most potent inhibitor of both enzymatic reactions catalyzed by Stx1. It is also a new type of mTOR inhibitor. The 4-aminopyrazolo[3,4-d]pyrimidines, a well-characterized class of compounds for tyrosine kinase inhibition, were used as a Src inhibitor module that blocks the adenosine binding site[1-2].

Chemical Properties

Light Tan Solid

Uses

4-Amino-1H-pyrazolo[3,4-d]pyrimidine decreases serum cholesterol markedly in rats.

Hazard

4-Aminopyrazolo[3,4-d]pyrimidine is harmful, irritating to the eyes and skin, and may cause respiratory irritation by inhalation. It is toxic if swallowed.

Synthesis

5399-92-8

2380-63-4

4-Chloro-1H-pyrazolo[3,4-d]pyrimidine (200 mg, 1.29 mmol) was used as starting material and dissolved in tetrahydrofuran (THF, 2.0 mL). Subsequently, ammonium hydroxide (2.0 mL) was added to this solution. The reaction mixture was stirred at 20 to 30 °C for 2 hours. After the reaction was completed, the mixture was concentrated. The concentrate was ground with acetonitrile (MeCN, 0.5 mL) and the product was subsequently collected by filtration to afford 4-aminopyrazolo[3,4-d]pyrimidine (37) as a red solid (100 mg, 57% yield).

References

[1] M Brigotti. “4-Aminopyrazolo[3,4-d]pyrimidine (4-APP) as a novel inhibitor of the RNA and DNA depurination induced by Shiga toxin 1.” Nucleic Acids Research 28 12 (2000): 2383–8.
[2] Ho Jin Lee. “Development of a 4-aminopyrazolo[3,4-d]pyrimidine-based dual IGF1R/Src inhibitor as a novel anticancer agent with minimal toxicity.” Molecular Cancer 17 1 (2018): 50.

4-Aminopyrazolo[3,4-d]pyrimidine

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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