Water → HCID 67329050, compound

Participants

Reaction Steps

To stirred solution containing 269 mg (0.52 mmol) of 5-(benzyloxy)-2-(2,5-dimethyl-1H-pyrrol-1-yl)-4-hexadecyl-6-methylpyrimidine in 10 mL of ethanol were added 723 mg (10.40 mmol) of hydroxylamine hydrochloride. The reaction mixture was then stirred at reflux during 5 h. The reaction mixture was then poured into 70 mL of water and then basified to a pH 9-10 with a 1N NaOH aqueous solution. The mixture was extracted with two 70-mL portions of ethyl acetate. The combined organic layer was washed with a 70-mL portion of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (10×3 cm). Elution with 3:2 hexanes-ethyl acetate afforded the expected product as a colorless oil: yield 231 mg (100%); silica gel TLC Rf 0.25 (1:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 0.85 (t, 3H, J=6.8 Hz), 1.26 (m, 26H), 1.61 (quint, 2H, J=7.2 Hz), 2.28 (s, 3H), 2.56 (dd, 2H, J=7.6, 7.6 Hz), 4.72 (s, 2H), 5.03 (br s, 2H) and 7.35-7.40 (m, 5H); 13C NMR (CDCl3) δ 14.08, 18.91, 22.66, 28.42, 29.33, 29.41, 29.52, 29.63, 29.63, 29.63, 29.63, 29.67, 29.67, 29.67, 29.67, 29.73, 31.90, 75.88, 127, 88, 128.24, 128.24, 128.58, 128.58, 136.79, 142.87, 158.79, 161.12 and 164.87; mass spectrum (APCI), m/z 440.3646 (M+H)+ (C28H46N3O requires 440.3641).

Provenance & Evidence