Water → HCID 69733509, compound

Participants

Reaction Steps

A mixture of (R)-3-(5-azidohexyl)-8-benzyl-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (380 mg, 0.90 mmol), triphenylphosphine (260 mg, 0.99 mmol), water (0.1 ml) and tetrahydrofuran (15 ml) was stirred at room temperature for 18 hours followed by heating at 500 C for 4 hours. Another portion of triphenylphosphine (100 mg) was added and the mixture was heated at 65° C. for 18 hours. After concentration under reduced pressure, the residue was treated with 1.0 M aqueous hydrochloric acid (10 ml) and ethyl acetate (10 ml), followed by extraction of the organic layer with 1.0 M aqueous hydrochloric acid (2×10 ml). The combined aqueous layers were made slightly basic (pH˜8) by addition of aqueous potassium hydroxide solution and extracted with ethyl acetate (2×20 ml). The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure to afford (R)-3-(5-aminohexyl)-8-benzyl-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (155 mg, 43% yield) as a beige powder. 1H NMR (300 MHz, CDCl3) δ 1.05 (d, 3H), 1.39 (broad s, 4H), 1.66 (m, 2H), 1.90 (broad s, 1H), 2.45 (s, 3H), 2.81 (broad s, 1H), 3.61 (s, 3H), 4.00 (t, 2H), 5.25 (s, 2H), 6.51 (s, 1H), 7.25-7.55 (m, 5H).

Provenance & Evidence