4-Methoxybenzylamine → HCID 86663605, compound

Participants

Reaction Steps

A stirred solution of compound 163 (14.30 g, 43.87 mmol) in DMSO (90 mL) was treated with slow addition of 4-methoxybenzylamine (57.3 mL, 482.52 mmol) under nitrogen at 70° C. The resultant mixture was stirred at 70 to 75° C. for 48 h, then cooled to room temperature and poured into a beaker of ice-water (1 L) with stirring. The resulted solid was collected by filtration, washed with water and dried in a vacuum oven (45° C.) for 2 h. The crude product was triturated with CH2Cl2 to provide N4-(4-fluoro-3-(trifluoromethyl)phenyl)-N6-(4-methoxybenzyl)pyrido[3,4-d]pyrimidine-4,6-diamine (166) (14.40 g, 74%) as a yellow solid, m.p. 202-204° C. 1H NMR [(CD3)2SO] δ 9.83 (s, 1H), 8.77 (s, 1H), 8.38 (s, 1H), 8.27-8.30 (m, 1H), 8.21-8.24 (m, 1H), 7.55 (t, J=9.7 Hz, 1H), 7.28-7.34 (m, 3H), 7.17 (s, 1H), 6.86-6.90 (m, 2H), 4.50 (d, J=6.3 Hz, 2H), 3.71 (s, 3H). Anal. Calcd for C22H17F4N5O: C, 59.59; H, 3.86; N, 15.79%. found: C, 59.31; H, 4.07; N, 15.46%.

Provenance & Evidence