Water → HCID 178493909, compound

Participants

Reaction Conditions

Reaction Steps

N-(8-Hydroxy-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyrimidine-5-carboxamide (Intermediate B, 4.2 g, 7.4 mmol) was diluted in dimethylformamide (75 mL). Cesium carbonate (12.1 g, 37.1 mmol) was added, followed by 2-{2-[(tert-butoxycarbonyl)amino]ethoxy}ethyl methanesulfonate (Step 2, 5.26 g, 18.6 mmol). The mixture was stirred at 50° C. overnight. After cooling to rt, water was added and the mixture was cooled to 0° C. for 30 min. The product was isolated by vacuum filtration, washing with water, and dried in the vacuum oven. The title compound was obtained as an orange solid (3.55 g, 91%). HPLC MS RT=2.23 min, MH+=525.1. 1H NMR (DMSO-d6+2 drops TFA-d) δ: 1.35 (9H, s), 3.07 (2H, t), 3.46 (2H, t), 3.81 (2H, m), 4.02 (3H, s), 4.25 (2H, m), 4.40 (2H, m), 4.57 (2H, m), 7.49 (1H, d), 7.85 (1H, m), 8.03 (1H, d), 8.82 (1H, m), 8.93 (1H, m), 9.48 (1H, m).

Provenance & Evidence