Pyridine → HCID 60123476, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (R)-1,7-dimethyl-3-(5-(N,N-dimethylamino)hexyl)pyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (315 mg, 0.947 mmol), pyridine (1 ml, 12.4 mmol) and dichloromethane (20 ml), cooled in an ice bath, was added trifluoromethanesulfonic anhydride (0.315 ml, 1.87 mmol) dropwise. After stirring for 2 hours, the cooling bath was removed. A 30% (v:v) solution of dimethylamine in tetrahydrofuran (7 ml) was added and the solution was transferred to a pressure tube (1″×8″). The tube was sealed and heated to 55° C. for 2 hours. After cooling to room temperature the solution was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the solution filtered through a pad of celite. The filtrate was rinsed with saturated sodium bicarbonate solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with ethyl acetate-methanol-triethylamine (85:10:5) to afford (R)-1,7-Dimethyl-5-(N,N-dimethylamino)-3-(5-(N,N-dimethylamino)hexyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)dione (300 mg, 88% yield for 2 steps) as an oil. 1H NMR (300 MHz, CDCl3) δ 0.99 (d, 3H), 1.20-1.50 (m, 3H), 1.52-1.74 (m, 3H), 2.28 (s, 6H), 2.42 (s, 3H), 2.99 (s, 6H), 3.64 (s, 3H), 4.03 (t, 2H), 6.39 (s, 1H).

Provenance & Evidence