5-Bromo-2-chloro-4-methoxypyrimidine

Description

5-bromo-2-chloro-4-Methoxypyrimidine is a building block used in the chemical synthesis of halogenated heterocycles.

Uses

5-Bromo-2-chloro-4-methoxypyrimidine is a building block in the chemical synthesis.

Synthesis

To a stirred solution of 5-bromo-2,4-dichloropyrimidine (500 mg, 2.19 mmol) in methanol (5 mL) was slowly added 30% sodium methanol solution (0.40 mL, 2.26 mmol). The reaction mixture was stirred at room temperature for 2 hours and then concentrated under reduced pressure. The residue was dissolved in water (5 mL) and extracted with ethyl acetate (3 x 5 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 5-bromo-2-chloro-4-methoxypyrimidine (432 mg, 88% yield) as a white solid.LCMS-ESI (m/z): C5H4BrClN2O Calculated value: 223.4; Measured value: 224.2 [M + H]+, tR = 7.66 min (Method 2) The following is a summary of the results.

References

[1] Patent: WO2011/76419, 2011, A1. Location in patent: Page/Page column 119
[2] Patent: EP2338888, 2011, A1. Location in patent: Paragraph 0173; 0174
[3] Tetrahedron Letters, 2006, vol. 47, # 26, p. 4415 - 4418
[4] Patent: CN106588884, 2017, A. Location in patent: Paragraph 0299; 0303; 0304; 0305
[5] Patent: WO2013/90454, 2013, A2. Location in patent: Paragraph 00386