Sodium Iodide → 4-Chloro-6-(5-iodo-2-ethoxy-phenyl)pyrimidin-2-ylamine

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To a solution of 4-chloro-6-(5-tributylstannyl-2-ethoxy-phenyl)pyrimidin-2-ylamine (79 mg, 0.13 mmol) in a 3% solution of acetic acid in ethanol (1 ml) was added a solution of sodium iodide (24 mg, 0.16 mmol) in a 0.1 M aqueous sodium hydroxide solution (0.2 ml) followed by a solution of chloramine-T (15.0 mg, 0.065 mmol) in water (0.15 ml). The orange solution was stirred at room temperature for 1 hour, treated with saturated aqueous sodium thiosulfate solution (0.3 ml), and extracted with ethyl acetate (2×1 ml). The combined extracts were concentrated under reduced pressure. The residue was purified by preparative TLC eluting with 20% ethyl acetate-hexane to provide 4-chloro-6-(5-iodo-2-ethoxy-phenyl)pyrimidin-2-ylamine (39 mg, 71% yield) as a white powder. 1H NMR (CDCl3) δ 8.24 (d, J=2.3 Hz, 1H), 7.67 (dd, J=2.3, 8.70 Hz, 1H), 7.38 (d, J=8.70 Hz, 2H), s, 1H), 6.76 (d, J=8.70 Hz, 1H), 5.23 (s, 1H), 4.13 (q, J=7.0 Hz, 2H), 1.47 (t, J=7.0 Hz, 3H).

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