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865156-67-8

865156-67-8 Structure

865156-67-8 Structure
IdentificationBack Directory
[Name]

6-BROMOIMIDAZO[1,2-A]PYRIMIDINE-3-CARBALDEHYDE
[CAS]

865156-67-8
[Synonyms]

CHEMMAKER CMFS-00344
6-BROMOIMIDAZO[1,2-A]PYRIMIDINE-3-CARBALDEHYDE
Imidazo[1,2-a]pyrimidine-3-carboxaldehyde, 6-bromo-
[Molecular Formula]

C7H4BrN3O
[MDL Number]

MFCD09994317
[MOL File]

865156-67-8.mol
[Molecular Weight]

226.03
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Synthesis]

2-Amino-5-bromopyrimidine

7752-82-1

2-Bromomalonaldehyde

2065-75-0

6-BROMOIMIDAZO[1,2-A]PYRIMIDINE-3-CARBALDEHYDE

865156-67-8

General procedure for the synthesis of 6-bromoimidazo[1,2-A]pyrimidine-3-carbaldehyde from 2-amino-5-bromopyrimidine and 2-bromomalonaldehyde: 2-bromomalonaldehyde (500 mg, 2.90 mmol) was added to a solution of 2-amino-5-bromopyrimidine (526 mg, 3.49 mmol) in acetonitrile (20 mL). The reaction mixture was heated to reflux for 2 hours. Upon completion of the reaction, the reaction was quenched with saturated sodium bicarbonate solution (20 mL) and extracted with ethyl acetate (3 × 20 mL). The organic layers were combined, washed with saturated brine (20 mL) and dried over anhydrous sodium sulfate. The organic layers were concentrated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography with gradient elution using chloroform/methanol (98:2 to 100:0, v/v) as eluent to afford the target product 6-bromoimidazo[1,2-A]pyrimidine-3-carbaldehyde. Yield: 40%; 1H NMR (DMSO-d6, 300 MHz): δ 9.98 (s, 1H), 9.75-9.76 (d, 1H, J = 2.4 Hz), 8.97-8.98 (d, 1H, J = 2.4 Hz), 8.70 (s, 1H); MS (m/z): 226 [M + H]+.

[References]

[1] Patent: WO2011/55320, 2011, A1. Location in patent: Page/Page column 50
[2] Chinese Chemical Letters, 2015, vol. 26, # 1, p. 118 - 120
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