Sodium Azide → HCID 86591000, compound

Participants

Reaction Steps

A mixture of the crude (S)-8-benzyl-1,7-dimethyl-3-(5-methanesulfonyloxyhexyl)pyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione, dimethylsulfoxide (6 ml) and sodium azide (116 mg, 1.79 mmol) was heated at 600 C for 18 hours. After cooling to room temperature, the mixture was partitioned between water (50 ml) and ethyl acetate (50 ml) and the aqueous layer was extracted with ethyl acetate (50 ml). The combined extracts were rinsed with water and with saturated aqueous sodium chloride solution. Concentrating under reduced pressure afforded (R)-3-(5-azidohexyl)-8-benzyl-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (380 mg, 99% yield for 2 steps) as an oil. 1H NMR (300 MHz, CDCl3) δ 1.22 (d, 3H), 1.36-1.60)m, 4H), 1.62-1.78 (m, 2H), 2.48 (s, 3H), 3.43 (m, 1H), 3.64 (s, 3H), 4.03 (t, 2H), 5.29 (s, 2H), 6.55 (s, 1H), 7.29

Provenance & Evidence