Sodium Carbonate → Benzenemethanol, 4-((2-amino-6-(5-chloro-2-ethoxyphenyl)-4-pyrimidinyl)amino)-

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To a mixture of [4-(2-amino-6-chloro-pyrimidin-4-yl-amino)-phenyl]-methanol (6.0 g, 24 mmol), 5-chloro-2-ethoxy-phenyl boronic acid (7.7 g, 38.4 mmol), palladium (II) acetate (0.54 g, 2.4 mmol) and triphenylphosphine (1.26 g, 4.8 mmol) was added a solution of sodium carbonate (12.7 g, 120 mmol) in water (80 ml) followed by glyme (300 ml). The mixture was stirred under an argon atmosphere at 95-105° C. for 18 hours. Filtration and concentration of the filtrate yielded a residue which was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3) to provide the title compound (5.5 g, 62% yield) as a white powder. 1H NMR (DMSO-d6) δ 1.38 (t, 3H, J=6.9 Hz, CH3), 4.13 (q, 2H, J=6.9 Hz, CH2), 4.45 (d, 2H, J=5.7 Hz, CH2), 5.07 (t, 1H, J=5.7 Hz, OH), 6.26 (s, 2H, NH2), 6.77 (s, 1H, Ar), 7.14 (d, 1H, J-8.9 Hz, Ar), 7.24 (d, 2H, J=8.4 Hz, Ar), 7.41 (dd, 1H, J=8.8, 2.8 Hz, Ar), 7.64 (d, 2H, J=8.3 Hz, Ar), 7.93 (d, 1H, J=2.8 Hz, Ar), 9.12 (s, 1H, NH).

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