Trimethylsilyl iodide → HCID 86267613, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-((6-(2-(isopropylamino)-4-methoxypyrimidin-5-yl)pyridin-3-yl)oxy)-N-methylpicolinamide (0.072 g, 0.183 mmol) in DCE (10 mL) was treated with iodotrimethylsilane (0.497 mL, 3.65 mmol), heated at 50° C. for 20 h, treated with additional iodotrimethylsilane (0.25 mL, 1.84 mmol) and heated at 60° C. for 20 h. The mixture was cooled to RT, treated with DCM/THF (5:1), washed with satd. NaHCO3, 10% sodium bisulfite, then brine. The combined aqueous washes were back-extracted with DCM/THF (5:1) (1×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified by preparatory TLC (EtOAc) to afford 4-((6-(2-(isopropylamino)-6-oxo-1,6-dihydropyrimidin-5-yl)pyridin-3-yl)oxy)-N-methylpicolinamide (16 mg, 23%). 1H NMR (400 MHz, DMSO-d6): δ 10.89 (br s, 1H), 8.79 (d, J=5.2 Hz, 1H), 8.66 (s, 1H), 8.52 (d, J=5.6 Hz, 1H), 8.47 (d, J=2.9 Hz, 1H), 8.44 (d, J=8.8 Hz, 1H), 7.67 (dd, J=8.8, 2.9 Hz, 1H), 7.42 (d, J=2.6 Hz, 1H), 7.21 (dd, J=5.6, 2.6 Hz, 1H), 6.74 (br s, 1H), 4.08 (m, 1H), 2.77 (d, J=4.8 Hz, 3H), 1.16 (d, J=6.5 Hz, 6H); MS (ESI) m/z: 381.2 (M+H+).

Provenance & Evidence