Potassium Iodide → HCID 24963596, compound

Participants

Reaction Steps

To a mixture of 6-fluoro-5-(2-fluoro-4-iodophenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione 17C (60 mg, 0.14 mmol, 1 eq) and potassium iodide (39 mg) in DMF (3 mL) was added cesium carbonate (135 mg, 0.42 mmol, 3 eq). The reaction mixture was stirred at ambient temperature for 5 minutes. 2-Bromoethanol (0.1 mL, 1.4 mmol, 10 eq) was then added and the reaction mixture was irradiated with microwave at 140° C. for 20 minutes. The reaction mixture was filtered and the filtrate was purified by preparatory LC/MS (30-55% CH3CN in H2O) to give 6-fluoro-5-(2-fluoro-4-iodophenylamino)-3-(2-hydroxyethyl)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (example 17) as an off-white solid (25 mg, 38% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.59 (s, 3 H) 3.67 (dd, J=2.53, 1.26 Hz, 2 H) 4.05 (t, J=5.05 Hz, 2 H) 4.98 (br. s., 1 H) 6.99 (td, J=8.65, 5.43 Hz, 1 H) 7.53 (dd, J=8.34, 0.76 Hz, 1 H) 7.68 (dd, J=10.36, 1.77 Hz, 1 H) 8.55 (s, 1 H) 10.22 (d, J=2.27 Hz, 1 H). [M+H] calc'd for C16H13F21N4O3, 475; found, 475.

Provenance & Evidence