HCID 67328968, compound → HCID 53373264, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 100 mg (0.21 mmol) 5-(benzyloxy)-4-hexadecyl-N,N,6-trimethylpyrimidin-2-amine in 5 mL of methanol were added 5 mg of 20% palladium hydroxide on carbon (Degussa type E101 NE/E). 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 (8×3 cm). Elution with 4:1 hexane-ethyl acetate afforded the expected product as white solid: yield 20 mg (25%); mp: 86-87° C.; silica gel TLC Rf 0.45 (4:1 hexanes-ethyl acetate); 1H NMR (methanol-d4) δ 0.89 (t, 3H, J=6.8 Hz), 1.28-1.34 (m, 26H), 1.67 (quint, 2H, J=7.2 Hz), 2.28 (s, 3H), 2.63 (dd, 2H, J=7.6, 7.6 Hz) and 3.07 (s, 6H); 13C NMR (methanol-d4) δ 12.96, 17.52, 22.27, 27.23, 29.00, 29.12, 29.12, 29.20, 29.20, 29.20, 29.30, 29.30, 29.30, 29.30, 29.30, 31.21, 31.61, 36.50, 36.50, 138.02, 155.61, 157.31 and 159.41; mass spectrum (APCI), m/z 378.3491 (M+H)+ (C23H44N3O requires 378.3484).

Provenance & Evidence