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3-Bromoimidazo[1,2-a]pyrimidine

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3-Bromoimidazo[1,2-a]pyrimidine Basic information
Uses
Product Name:3-Bromoimidazo[1,2-a]pyrimidine
Synonyms:3-BROMOIMIDAZO[1,2-A]PYRIMIDINE;3-BROMOIMIDAZOL-(1,2-A)-PYRIMIDINE;Imidazo[1,2-a]pyrimidine, 3-bromo-;3-Bromoimidazo[1,2-a]pyrimidine ISO 9001:2015 REACH;-Bromoimidazo[1,2-a]pyrimidine;3-Bromoimidazo[1,2-a]pyrimidine 98%
CAS:6840-45-5
MF:C6H4BrN3
MW:198.02
EINECS:
Product Categories:Fused Ring Systems;Halides;Fluorobenzene;Pyrimidines;Heterocycle-Pyrimidine series
Mol File:6840-45-5.mol
3-Bromoimidazo[1,2-a]pyrimidine Structure
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
pka2.55±0.30(Predicted)
color Light brown
InChIInChI=1S/C6H4BrN3/c7-5-4-9-6-8-2-1-3-10(5)6/h1-4H
InChIKeyGNHZXUKWLSWKHB-UHFFFAOYSA-N
SMILESC12=NC=C(Br)N1C=CC=N2
CAS DataBase Reference6840-45-5(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,T
Risk Statements 25
Safety Statements 45
HazardClass IRRITANT
HS Code 2933998090
MSDS Information
3-Bromoimidazo[1,2-a]pyrimidine Usage And Synthesis
Uses3-Bromoimidozolo[1,2-a]pyrimidine can be used to prepare HPK1 inhibitors.
Synthesis
Imidazo[1,2-a]pyrimidine

274-95-3

3-Bromoimidazo[1,2-a]pyrimidine

6840-45-5

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
3-Bromoimidazo[1,2-a]pyrimidine Preparation Products And Raw materials
Raw materialsImidazo[1,2-a]pyrimidine-->Methanol-->Sodium acetate
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