Hydrochloric Acid → HCID 60123474, compound

Participants

Reaction Steps

37% Aqueous hydrochloric acid (5 ml) was added to a solution of the crude (R)-3-(5-acetoxyhexyl)-8-benzyl-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione in methanol (20 ml). After stirring at room temperature for 18 hours, the solution was concentrated under reduced pressure. The residue was treated with water (20 ml) and extracted with ethyl acetate (2×20 ml). The combined extracts were concentrated under reduced pressure to provide an oil which solidified on standing. The solid was recrystallized (ethyl acetate-hexanes) to afford (R)-8-Benzyl-1,7-dimethyl-3-(5-hydroxyhexyl)pyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (1.26 g, 60% yield for 2 steps) as a white powder. 1H NMR (300 MHz, CDCl3) δ 1.19 (d, 3H), 1.35-1.52 (m, 4H), 1.54-1.70 (m, 2H), 2.47 (s,3H), 3.63 (s, 3H), 3.78 (m, 1H), 4.05 (t, 2H), 5.29 (s, 2H), 6.54 (s, 1H), 7.25-7.55 (m, 5H).

Provenance & Evidence