HCID 67327786, compound → HCID 66553675, compound

Participants

Reaction Steps

To a stirred solution containing 113 mg (0.27 mmol) of 5-(benzyloxy)-6-(10-(methoxymethoxy)decyl)-4-methylpyridin-2-amine in 10 mL of methanol were added two drops of concentrated HCl and the mixture was stirred at reflux for 16 h. To the mixture were added 5 mg of 20% palladium hydroxide on carbon (Degussa type E101 NE/N). The reaction mixture was stirred at 23° C. under hydrogen atmosphere for 15 min. The reaction mixture was filtered through celite and the filtrated was concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (10×1 cm). Elution with 17:3 dichloromethane-methanol afforded the expected product as white solid: yield 22 mg (29%); mp: 138-139° C.; silica gel TLC Rf 0.20 (17:3 dichloromethane-methanol); 1H NMR (methanol-d4) δ 1.28-1.35 (m, 12H), 1.48-1.58 (m, 4H), 2.13 (s, 3H), 2.60 (dd, 2H, J=7.6, 7.6 Hz), 3.51 (t, 2H, J=6.8 Hz) and 6.25 (s, 1H); 13C NMR (methanol-d4) δ 15.21, 25.51, 28.78, 29.15, 29.20, 29.22, 29.22, 29.28, 31.49, 32.23, 61.58, 108.39, 139.23, 141.68, 146.88 and 152.45; mass spectrum (APCI+), m/z 281.2231 (M+H) (C16H29N2O2 requires 281.2229).

Provenance & Evidence