6-BROMO-PYRAZOLO[1,5-A]PYRIMIDINE Chemical Properties

Melting point:

122-124℃

Density 

1.89±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

-0.81±0.30(Predicted)

color 

Light yellow

Water Solubility 

Slightly soluble in water.

Sensitive 

Light Sensitive

InChI

InChI=1S/C6H4BrN3/c7-5-3-8-6-1-2-9-10(6)4-5/h1-4H

InChIKey

VDHTXLUCUNPVLO-UHFFFAOYSA-N

SMILES

C12=CC=NN1C=C(Br)C=N2

Safety Information

HS Code 

2933599590

6-BROMO-PYRAZOLO[1,5-A]PYRIMIDINE Usage And Synthesis

Uses

6-Bromopyrazolo[1,5-a]pyrimidine is a reactant in the synthesis of LDN-212854, a selective and potent inhibitor of the BMP type I receptor kinases.

Synthesis

Using 2-bromomalonaldehyde (15.1 g, 100 mmol) and 3H-pyrazol-3-amine (8.3 g, 100 mmol) as raw materials, 120 mL of ethanol was added to a 250 mL round bottom flask and the mixture was cooled down to 0 °C. Subsequently, 12 mL of concentrated hydrochloric acid was slowly added and after returning to room temperature, stirring was continued for 2 hours. During the reaction, a yellowish solid precipitated. Upon completion of the reaction, the solid was collected by direct filtration and the filter cake was washed sequentially with saturated NaHCO3 solution and distilled water. After drying, 17 g of the intermediate 6-bromopyrazolo[1,5-a]pyrimidine was obtained in 86% yield.

References

[1] Patent: CN105130991, 2017, B. Location in patent: Paragraph 0037; 0041-0043
[2] Patent: WO2014/138088, 2014, A1. Location in patent: Page/Page column 60
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 15, p. 4388 - 4392
[4] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 23, p. 5830 - 5835

6-BROMO-PYRAZOLO[1,5-A]PYRIMIDINE(705263-10-1)Related Product Information

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