Water → HCID 67329697, compound

Participants

Reaction Steps

To stirred solution containing 533 mg (1.46 mmol) of 5-(benzyloxy)-2-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methyl-6-pentylpyrimidine in 10 mL of ethanol-water 9:1 were added 1.0 g (14.60 mmol) of hydroxylamine hydrochloride. The reaction mixture was then stirred at reflux during 5 h. A second portion of 1.0 g (14.60 mmol) of hydroxylamine hydrochloride was added and the reaction mixture was stirred at reflux for 16 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 2:1 hexanes-ethyl acetate afforded the expected product as a colorless oil: yield 334 mg (80%); silica gel TLC Rf 0.25 (2:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 0.86 (t, 3H, J=6.8 Hz), 1.27 (m, 4H), 1.63 (m, 2H), 2.28 (s, 3H), 2.56 (dd, 2H, J=8.0, 8.0 Hz), 4.71 (s, 2H), 5.15 (br s, 2H) and 7.35-7.37 (m, 5H); 13C NMR (CDCl3) δ 13.94, 18.85, 22.41, 28.04, 31.86, 75.90, 127.90, 128.26, 128.26, 128.58, 128.58, 136.76, 142.80, 156.18, 158.79, 161.13 and 164.89; mass spectrum (APCI), m/z 286.1914 (M+H)+ (C34H52N3O requires 286.1919).

Provenance & Evidence