2-AMINO-5-BROMO-4-METHOXYPYRIMIDINE Chemical Properties

Melting point:

118℃

Boiling point:

364.8±45.0 °C(Predicted)

Density 

1.723

storage temp. 

2-8°C(protect from light)

pka

3.82±0.10(Predicted)

Appearance

Off-white to light yellow Solid

2-AMINO-5-BROMO-4-METHOXYPYRIMIDINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-amino-5-bromo-4-methoxypyrimidine from 2-amino-4-methoxypyrimidine: Method 14; Synthesis of 5-bromo-4-methoxypyrimidin-2-ylamine; To a solution of 4-methoxypyrimidin-2-ylamine (1.84 g, 14.7 mmol) in chloroform (600 mL) was added N-bromosuccinimide (2.62 g, 14.7 mmol). The reaction mixture was stirred under light-avoiding conditions for 5 h. The reaction solution was transferred to a mixture of dichloromethane (200 mL) and 1N sodium hydroxide solution (100 mL). After thorough mixing, the organic and aqueous phases were separated, and the organic phase was washed with saturated sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 2.88 g (96% yield) of the target compound 5-bromo-4-methoxypyrimidin-2-ylamine.LCMS (m/z): 204/206 (MH+).1H NMR (CDCl3): δ 8.10 ( s, 1H), 4.93 (bs, 2H), 3.96 (s, 3H).

References

[1] Patent: WO2008/98058, 2008, A1. Location in patent: Page/Page column 66
[2] Patent: WO2007/84786, 2007, A1. Location in patent: Page/Page column 99-100
[3] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 10, p. 774 - 779
[4] Patent: WO2009/93981, 2009, A1. Location in patent: Page/Page column 104-105
[5] Journal of the American Chemical Society, 1946, vol. 68, p. 1039,1040, 1044

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