Methanol → HCID 53475812, compound

Participants

Reaction Conditions

Reaction Steps

Commercially available 4-aminomethylpyridine (2 g, 20.8 mmol) was dissolved in 60 ml of AcOEt and at 0° C. triphosgene (5.8 g, 21 mmol) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and the residue was dissolved in 20 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1a (3.16 g, 21 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt 9.5/MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (80 ml) and washed with water (1×40 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 640 mg of a white solid. Yield=11% 1HNMR (DMSO, 200 MHz) δ 4.34 (2H, d, J=5.8 Hz), 6.62 (1H, dd, J=7.6 Hz, J′=1 Hz), 6.92 (3H, m), 7.31 (2H, dd, J=4.4 Hz, J′=1.4 Hz), 8.49 (3H, m), 10.03 (1H, bs), 10.59 (1H, bs); [M+1] 284.1 (C14H13N5O2 requires 283.29).

Provenance & Evidence