4-Methoxybenzylamine → HCID 10647359, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 162 (13.9 g, 41.3 mmol) and 4-methoxybenzylamine (54.3 mL, 413 mmol) in dry DMSO (100 mL) was stirred under a nitrogen atmosphere at 75° C. (bath temperature) for 95 h. The solution was then cooled and petroleum ether (500 mL) was added. After 15 min stirring at room temperature the layers were allowed to separate and the petroleum ether layer was decanted. This procedure was repeated a further two times and then water (500 mL) was added to the resultant DMSO layer and the mixture was stirred at room temperature for 1 h to precipitate a yellow/orange solid that was collected by filtration and washed with water (5×100 mL), before being dried under vacuum and then washed with petroleum ether (2×100 mL). The yellowish orange solid was then stirred with warm acetone (1 L) for ca. 3 h before water (1 L) was added to precipitate the required product. The solid was collected by filtration, washed with acetone/water (1:1, 5×80 mL) and dried in vacuo over silica-gel, to give pure N4-(3-bromo-4-fluorophenyl)-N6-(4-methoxybenzyl)pyrido[3,4-d]pyrimidine-4,6-diamine (165) (14.8 g, 79%) as a yellow/orange solid, mp 181-184° C.; 1H NMR δ [(CD3)2SO] 9.69 (s, 1H), 8.75 (s, 1H), 8.37 (s, 1H), 8.26 (dd, J=6.4, 2.6 Hz, 1H), 7.91-7.83 (m, 1H), 7.42 (t, J=8.8 Hz, 1H), 7.33 (br d, J=8.6 Hz, 2H), 7.27 (t, J=6.3 Hz, 1H), 7.16 (s, 1H), 6.91-6.85 (m, 2H), 4.49 (d, J=6.3 Hz, 2H), 3.71 (s, 3H). Anal. Calcd for C21H17BrFN5O: C, 55.52; H, 3.77; N, 15.42%. Found C, 55.75; H, 3.88; N, 15.44%.

Provenance & Evidence