Sodium Carbonate → 2-Amino-4-chloro-6-(2-methyl-5-bromo-phenyl)-pyrimidine

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Reaction Steps

To a mixture of 2-methyl-5-bromo-phenylboronic acid (7.0 g, 32.6 mmol), 2-amino-4,6-dichloropyrimidine (6.95 g, 42.4 mmol), and degassed ethylene glycol dimethyl ether (150 ml) was added a solution of sodium carbonate (17.3 g, 163 mmol) in water (50 ml). The mixture was stirred vigorously and palladium acetate (0.73 g, 3.26 mmol) was added followed by triphenylphosphine (1.71 g, 6.52 mmol). After stirring for 16 hours, the mixture was diluted with water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with water (100 ml), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:4) to provide 2-amino-4-chloro-6-(2-methyl-5-bromo-phenyl)-pyrimidine (7.8 g, 80% yield) as a pale yellow powder. 1H NMR (DMSO-d6) δ 7.58 (d, J=2.0 Hz, 1H), 7.55 (dd, J=2.0, 8.1 Hz, 1H), 7.28 (d, J=8.1 Hz, 1H), 7.26 (br s, 2H), 6.86 (s, 1H), 2.32 (s, 3H).

Provenance & Evidence