HCID 67328276, compound → HCID 53373263, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 150 mg (0.48 mmol) 5-(benzyloxy)-4-decyl-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 33 mg (28%); mp: 71-72° C.; silica gel TLC Rf 0.25 (4:1 hexanes-ethyl acetate); 1H NMR (methanol-d4) δ 0.87 (t, 3H, J=6.8 Hz), 1.21-1.31 (m, 14H), 1.65 (quint, 2H, J=7.2 Hz), 2.26 (s, 3H), 2.62 (dd, 2H, J=7.2, 7.2 Hz) and 3.05 (s, 6H); 13C NMR (methanol-d4) δ 13.01, 17.55, 22.29, 27.27, 29.02, 29.15, 29.17, 29.26, 29.29, 31.24, 31.64, 36.52, 36.52, 138.04, 155.59, 157.31 and 159.41; mass spectrum (APCI), m/z 294.2554 (M+H)+ (C17H32N3O requires 294.2545).

Provenance & Evidence