7-Bromoquinazoline Chemical Properties

Boiling point:

304.3±15.0 °C(Predicted)

Density 

1.656±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

3.60±0.70(Predicted)

Appearance

White to yellow Solid

Safety Information

Risk Statements 

41

Safety Statements 

26-39

7-Bromoquinazoline Usage And Synthesis

Uses

7-Bromoquinazoline has been used as a reactant in the preparation of N1-(5-(heterocyclyl)-thiazol-2-yl)-3-(4-trifluoromethylphenyl)-1,2-propanediamines as AKT/PKB inhibitors for cancer treatment.

Synthesis

General procedure for the synthesis of 7-bromoquinazoline from quinazoline: Step A: N-bromosuccinimide (NBS, 2.13 g, 11.9 mmol) was slowly added to a solution of concentrated sulfuric acid (appropriate amount) of compound 214 (quinazoline, 1.04 g, 7.99 mmol) at room temperature. The reaction mixture was stirred continuously at room temperature for 16 h. The reaction progress was monitored by thin layer chromatography (TLC, unfolding agent: 5% methanol/dichloromethane) to confirm the completion of the reaction. Subsequently, the reaction mixture was carefully poured into crushed ice (~50 mL) and the pH was adjusted to neutral (pH=7) using ammonium hydroxide solution. The resulting slurry was continued to be stirred at 0 °C for 1 h. The solid product was then collected by filtration and washed with ice-cold water (3 x 30 mL). Finally, purification by silica gel column chromatography (SiO2, eluent: 5% methanol/dichloromethane) afforded the target compound 215 (7-bromoquinazoline) as a beige solid with a yield of 0.53 g in 32% yield. Product characterization: 1H NMR (400 MHz, DMSO-d6) δ 9.57 (s, 1H), 9.32 (s, 1H), 8.46 (d, 1H), 8.14 (dd, 1H), 7.96 (d, 1H).

References

[1] Patent: WO2008/82487, 2008, A2. Location in patent: Page/Page column 106
[2] Synthesis, 2002, # 1, p. 83 - 86

7-Bromoquinazoline(89892-22-8)Related Product Information

• Cefazolin sodium salt
• Cefazolin
• Quinazoline
• 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one
• ethyl 7-bromoquinoline-2-carboxylate
• 7-BroMoquinoline-2-carboxylic acid
• 7-broMoquinoline-3-carbaldehyde
• 7-BROMOQUINAZOLIN-2(1H)-ONE
• 7-BroMoquinoline-8-carboxylic acid
• 7-BROMOQUINOLINE-3-CARBOXYLIC ACID
• 7-broMoquinolin-3-aMine
• Ethyl 7-broMoquinoline-3-carboxylate
• Oxymetazoline hydrochloride
• 7-BROMO-4-CHLOROQUINAZOLINE
• 6-BROMO-2,4(1H,3H)-QUINAZOLINEDIONE
• 6-Bromoquinazolin-4-ol
• 6-BROMO-QUINAZOLIN-4-YLAMINE
• 7-BROMO-4-CHLORO-2-METHYLQUINAZOLINE