5-BROMO-2-PHENYLPYRIMIDINE Chemical Properties

Melting point:

83-84 °C(Solv: ethyl acetate (141-78-6))

Boiling point:

232.1±23.0 °C(Predicted)

Density 

1.493±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-0.39±0.22(Predicted)

Appearance

White to off-white Solid

5-BROMO-2-PHENYLPYRIMIDINE Usage And Synthesis

Synthesis

Step 1: Synthesis of 5-bromo-2-phenylpyrimidine First, 1.97 g of 5-bromo-2-iodopyrimidine, 0.85 g of phenylboronic acid, 7.0 mL of 2 M aqueous sodium carbonate and 18 mL of toluene were added to a 200 mL three-necked flask fitted with a reflux condenser tube, and the atmosphere in the flask was replaced with nitrogen. After the mixture was degassed by stirring under reduced pressure, 0.081 g of tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(PPh3)4) was added and the mixture was refluxed for 8 hours. Subsequently, 0.040 g of Pd(PPh3)4 was added and refluxing was continued for 8 h. Finally, 0.040 g of Pd(PPh3)4 was added and further refluxed for 8 h to complete the reaction. After completion of the reaction, water was added to the resulting solution and the organic layer was extracted with dichloromethane. The extract was washed with saturated brine and dried by adding magnesium sulfate. The dried solution was filtered and the solvent was removed by distillation. The resulting residue was purified by fast column chromatography using hexane and ethyl acetate (5:1, v/v) as the unfolding agent to afford the target pyrimidine derivative (white powder) in 59% yield. The synthetic scheme of step 1 is shown in (b-1) below.

References

[1] Organic Letters, 2002, vol. 4, # 4, p. 513 - 516
[2] Patent: WO2009/21696, 2009, A1. Location in patent: Page/Page column 52-53
[3] Patent: US2015/349278, 2015, A1
[4] Patent: JP2016/6041, 2016, A. Location in patent: Paragraph 0250; 0251-0253
[5] Patent: US2008/64697, 2008, A1. Location in patent: Page/Page column 27

5-BROMO-2-PHENYLPYRIMIDINE(38696-20-7)Related Product Information

• 4,5-DIBROMO-2,6-DIPHENYLPYRIMIDINE
• 5-BROMO-4-HYDRAZINO-2,6-DIPHENYLPYRIMIDINE
• 5-BROMO-4-CHLORO-2-PHENYLPYRIMIDINE
• 5-BROMO-2-PHENYLPYRIMIDINE
• 5-bromo-2-phenylpyrimidin-4-ol
• 5-BROMO-2-PHENYL-PYRIMIDIN-4-YLAMINE
• 5-BROMO-2-[4-(TRIFLUOROMETHYL)PHENYL]PYRIMIDIN-4-AMINE