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Imidazo[1,2-a]pyrimidine

Imidazo[1,2-a]pyrimidine structure

CAS No:
274-95-3
Formula:
C6H5N3
Chemical Name:
Imidazo[1,2-a]pyrimidine
Synonyms:
imidazo(1,2-a)pyrimidine;Imidazo[1,2-a]pyrimidine;1,3a,7-Triazaindene;Imidazo[1,2-a]pyrimidine HCl;1,8-Diazaindolizine;8-Azapyrimidazole;3,4-Diazaindolizine;PubChem14838;ACMC-1CHX0
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Imidazo[1,2-a]pyrimidine Basic Attributes

Molecular Weight：

119.127

Exact Mass：

119.048347

DSSTox ID：

DTXSID80341928

HScode：

2933990090

Characteristics

PSA：

30.2

XLogP3：

1.1

Density：

1.3±0.1 g/cm3

Melting Point：

127-129ºC

Refractive Index：

1.689

Safety Information

hazard class code：

safety instructions：

36/37

Marks：

Xi: Irritant;

Precautionary statement(s)：

P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362

Hazard Statements：

H315

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Drug Information

MeSH Entry Terms：

imidazo(1,2-a)pyrimidine

Imidazo[1,2-a]pyrimidine Use and Manufacturing

In a 250 ml three-neck round bottom flask, 2-aminopyrimidine (5 g), Bromoacetaldehyde diethyl acetal (20.7 g), 48percent aqueous solution of bromic acid (5 ml)Ethanol (50 ml) was added and the mixture was refluxed with stirring for 18 hours. The reaction solution was cooled to room temperature Silica gel was adsorbed. Through column separation using dichloromethane and methanol5 g of the title compound was obtained.In a 250 ml three-neck round bottom flask, 2-aminopyrimidine (5 g), Bromoacetaldehyde diethyl acetal (20.7 g), 48percent aqueous solution of bromic acid (5 ml)Ethanol (50 ml) was added and the mixture was refluxed with stirring for 18 hours. The reaction solution was cooled to room temperature Silica gel was adsorbed. Through column separation using dichloromethane and methanol5 g of the title compound was obtained.General procedure: Imidazo[1, 2-a]pyrimidine (0.3 mmol), 2-chlorobenzaldehyde (0.9 mmol, 3 equiv.), K2CO3 (0.9 mmol, 3 equiv.), NBu4Br (0.3 mmol, 1 equiv.), PivOH (30 molpercent), Pd(OAc)2 (5 mol percent), and Xantphos (10 mol percent) were added to a 10 mL round-bottomed flask, and then a mixed solvent of 3 mL of PhNO2 and 30 uL of H2O was added. The mixture was stirred under air at 110 °C for 24 h. After the reaction was complete, the mixture was washed with water and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo. The crude product was purified by flash chromatography on silica gel using dichloromethane/methanol as the eluent to give the pure product.General procedure: Imidazo[1, 2-a]pyrimidine (0.3 mmol), 2-chlorobenzaldehyde (0.9 mmol, 3 equiv.), K2CO3 (0.9 mmol, 3 equiv.), NBu4Br (0.3 mmol, 1 equiv.), PivOH (30 molpercent), Pd(OAc)2 (5 mol percent), and Xantphos (10 mol percent) were added to a 10 mL round-bottomed flask, and then a mixed solvent of 3 mL of PhNO2 and 30 uL of H2O was added. The mixture was stirred under air at 110 °C for 24 h. After the reaction was complete, the mixture was washed with water and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo. The crude product was purified by flash chromatography on silica gel using dichloromethane/methanol as the eluent to give the pure product.

Computed Properties

Molecular Weight:119.12
XLogP3:1.1
Hydrogen Bond Acceptor Count:2
Exact Mass:119.048347172
Monoisotopic Mass:119.048347172
Topological Polar Surface Area:30.2
Heavy Atom Count:9
Complexity:105
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Imidazo[1,2-a]pyrimidine CAS NO.274-95-3

CAS No.: 274-95-3

Grade: Industrial Grade

Content: 98%

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CAS No.: 274-95-3

Grade: Industrial Grade

Content: 98%

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