3-Bromoimidazo[1,2-a]pyrimidine Chemical Properties

Melting point:

158-160

Density 

1.89±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

pka

2.55±0.30(Predicted)

color 

Light brown

InChI

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

InChIKey

GNHZXUKWLSWKHB-UHFFFAOYSA-N

SMILES

C12=NC=C(Br)N1C=CC=N2

CAS DataBase Reference

6840-45-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25

Safety Statements 

45

HazardClass 

IRRITANT

HS Code 

2933998090

3-Bromoimidazo[1,2-a]pyrimidine Usage And Synthesis

Uses

3-Bromoimidozolo[1,2-a]pyrimidine can be used to prepare HPK1 inhibitors.

Synthesis

Imidazo[1,2-a]pyrimidine (4 g) and sodium acetate (4.3 g) were dissolved in methanol (40 ml) in a 100 ml three-necked round-bottomed flask, followed by cooling the reaction mixture to -10°C. Bromine (5.38 g) was added slowly and dropwise with stirring. Upon completion of the reaction, 1M aqueous sodium sulfide (40 ml) was added to quench the reaction and the mixture was subsequently concentrated under reduced pressure to remove the solvent. Liquid-liquid extraction was carried out via ethyl acetate and water to separate the by-products, and finally the crude product was purified by column chromatography using dichloromethane and methanol as eluents to give 3.2 g of 3-bromoimidazo[1,2-a]pyrimidine.

References

[1] European Journal of Medicinal Chemistry, 1991, vol. 26, # 1, p. 13 - 18
[2] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 5, p. 1170 - 1176
[3] Patent: KR2017/126059, 2017, A. Location in patent: Paragraph 0069; 0072; 0073; 0078; 0079

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