4-Methoxybenzylamine → HCID 86663608, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 164 (8.90 g, 33.7 mmol) and 4-methoxybenzylamine (44.2 mL, 337 mmol) in dry DMSO (80 mL) was stirred under nitrogen at 70° C. (bath temperature) for 158 h. The resultant solution was cooled briefly and then stirred with petroleum ether (2×400 mL) at room temperature for 15 min before the petroleum ether layer was decanted. Water (400 mL) was added to the DMSO layer and the mixture was stirred at room temperature for 3 h. The solid thus precipitated was collected by filtration and washed with water (5×100 mL), before being suctioned dry and then washed with petroleum ether (2×100 mL) and suctioned dry again. The resultant brownish orange solid was dissolved in warm acetone (400 mL) and water (500 mL) was added. The mixture was then stirred at room temperature for 1 h and the resultant solid was collected by filtration, washed with acetone/water (1:1, 5×80 mL) and dried in vacuo over silica-gel, to give N4-(3-ethynylphenyl)-N6-(4-methoxybenzyl)pyrido[3,4-d]pyrimidine-4,6-diamine (167) (10.3 g, 80%) as a yellow/orange solid, mp 200-203° C.; 1H NMR δ [(CD3)2SO] 9.63 (s, 1H), 8.75 (s, 1H), 8.38 (s, 1H), 8.03 (br s, 1H), 7.94-7.88 (m, 1H), 7.41 (t, J=7.9 Hz, 1H), 7.34 (br d, J=8.6 Hz, 2H), 7.28-7.21 (m, 2H), 7.19 (s, 1H), 6.92-6.85 (m, 2H), 4.50 (d, J=6.3 Hz, 2H), 4.19 (s, 1H), 3.71 (s, 3H). Anal. Calcd for C23H19N5O: C, 72.42; H, 5.02; N, 18.36%. Found C, 72.28; H, 5.05; N, 18.22%.

Provenance & Evidence