Anisole → HCID 86663606, compound

Participants

Reaction Steps

A stirred solution of compound 166 (1.0 g, 2.26 mmol) in TFA (20 mL) was treated with anisole (490 μL, 4.51 mmol) at room temperature. The mixture was stirred overnight, then diluted with ethyl acetate and the solvents were removed under reduced pressure. The residue was triturated with hexane and then treated with aqueous ammonia (5N, 100 mL) with stirring for 30 min. The resulting solid was collected by filtration, washed with water and dried under vacuum to give N4-(4-fluoro-3-(trifluoromethyl)phenyl)pyrido[3,4-d]pyrimidine-4,6-diamine (168) (720 mg, 99%) as a yellow solid, m.p. 252-255° C. 1H NMR [(CD3)2SO] δ 9.90 (s, 1H), 8.72 (s, 1H), 8.38 (s, 1H), 8.34 (dd, J=6.5, 2.6 Hz, 1H), 8.24-8.28 (m, 1H), 7.54 (t, J=9.7 Hz, 1H), 7.14 (s, 1H), 6.30 (s, 2H). Anal. Calcd for C14H9F4N5.0.55EtOAc: C, 52.35; H, 3.63; N, 18.84%. found: C, 51.96; H, 3.70; N, 18.46%.

Provenance & Evidence