2-Amino-6-methyl-4-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-one Chemical Properties

Melting point:

161.8-163 °C

Boiling point:

459.9±28.0 °C(Predicted)

Density 

1.44±0.1 g/cm3(Predicted)

vapor pressure 

0.004Pa at 25℃

storage temp. 

2-8°C

solubility 

DMSO: 13 mg/mL

pka

2.96±0.40(Predicted)

form 

solid

color 

white

Water Solubility 

5.7g/L at 20℃

InChIKey

UQDVRVNMIJAGRK-UHFFFAOYSA-N

LogP

0.49 at 20℃

CAS DataBase Reference

27277-00-5(CAS DataBase Reference)

EPA Substance Registry System

2-Amino-4,5-dihydro-6-methyl-4-propyl-s-triazolo-(1,5-a)-pyrimidin-5-one (27277-00-5)

Safety Information

RIDADR 

2811

WGK Germany 

1

HazardClass 

6.1(b)

PackingGroup 

III

MSDS

• Language:English Provider:SigmaAldrich

2-Amino-6-methyl-4-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-one Usage And Synthesis

Uses

ICI 63197 is a specific cAMP phosphodiesterase (PDE) inhibitor. It is potent in anatagonizing reserpine-induced hypothermia. potent PDE4 inhibitor.

Definition

ChEBI: 2-amino-6-methyl-4-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-one is a member of triazolopyrimidines.

Flammability and Explosibility

Not classified

Biological Activity

Potent phosphodiesterase (PDE) 4 inhibitor (IC 50 = 35 nM for inhibition of [ 3 H]-rolipram binding to rat brain). Antidepressant following systemic administration in vivo .

Biochem/physiol Actions

Phosphodiesterase IV (PDE 4) inhibitor

Synthesis

2-Amino-6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-one (165 g, 1 mol) and bromopropane (184 g, 1.5 mol) were added to the reaction apparatus, followed by triethylamine (101 g, 1 mol) and chloroform (900 mL). The reaction mixture was heated to 65 °C and maintained at this temperature for 6 hours. The progress of the reaction was monitored by HPLC until the amount of 2-amino-6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-one was less than 0.5%. After completion of the reaction, the chloroform was recovered by distillation at 50 °C. Ethyl acetate (830 mL) and water (330 mL) were added to the residue and the organic phase was separated by stirring. After distillation to remove some of the ethyl acetate (~500mL), the remaining solution was crystallized. The crystals were collected by filtration and washed with water until the wash solution was neutral. Finally, dried to constant weight at 70 °C to afford 2-amino-6-methyl-4-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one (176 g, 85% yield, 99% purity).

storage

+4°C

References

[1] Patent: CN107602563, 2018, A. Location in patent: Paragraph 0028; 0029; 0030; 0031; 0032; 0033; 0034-0044

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• 2-Amino-6-methyl-4-propyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-one