4-Aminopyrazolo[3,4-d]pyrimidine 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

pka

12.12±0.20(Predicted)

form 

powder to crystal

color 

White to Orange to Green

Water Solubility 

Insoluble in water.

BRN 

5824

InChIKey

LHCPRYRLDOSKHK-UHFFFAOYSA-N

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 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29335990

Toxicity

LD50 oral in rat: 141mg/kg

MSDS

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4-Aminopyrazolo[3,4-d]pyrimidine 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

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.

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