N,N-Dimethylglycine → Methyl {4-[4-(4-amino-5-oxo-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-6(5H)-yl)phenoxy]phenyl}acetate

Participants

Reaction Steps

A stirred slurry of 4-amino-6-(4-iodophenyl)-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-5(6H)-one (38 mg, 0.10 mmol), methyl 4-hydroxyphenylacetic acid (25 mg, 0.15 mmol), cesium carbonate (78 mg, 0.24 mmol), N,N-dimethyl glycine (10.3 mg, 0.10 mmol) and copper (I) iodide (6 mg, 0.03 mmol) in p-dioxane (0.4 mL) were heated at 90° C. for 18 hours. The reaction mixture was cooled, concentrated in vacuo and chromatographed (0-5% methanol: chloroform) to afford the title compound as a solid, 2.4 mg. 1H NMR (400 MHz, CDCl3) δ 8.31 (s, 1H), 7.25 (d, 2H), 7.20 (d, 2H), 7.07 (d, 2H), 7.02 (d, 2H), 4.69 (m, 2H), 4.00 (m, 2H), 3.68 (s, 3H). m/z=421.2 (M+1). IC50 254 nM.

Provenance & Evidence