Potassium Hydroxide → HCID 67328269, compound

Participants

Reaction Steps

To a stirred solution containing 230 mg (0.47 mmol) of 5-(benzyloxy)-2-(2,5-dimethyl-1H-pyrrol-1-yl)-4-(10-(methoxymethoxy)decyl)-6-methylpyrimidine in 15 mL of 9:1 ethanol-water was added 327 mg (4.70 mmol) of hydroxylamine hydrochloride followed by 263 mg (4.70 mmol) of KOH. The reaction mixture was then heated and stirred at reflux for 5 h. A second portion of 327 mg (4.70 mmol) of hydroxylamine hydrochloride followed by 263 mg (4.70 mmol) of KOH was added and the reaction mixture was heated and stirred at reflux for 12 h. The reaction mixture was poured into 70 mL of water and then treated with 1N NaOH until pH 9-10 was reached. The reaction mixture was extracted with two 70-mL portions of ethyl acetate. The combined organic layer was washed with 70 mL of brine, dried (MgSO4) and 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 133 mg (76%); silica gel TLC Rf 0.76 (9:1 dichloromethane-methanol); 1H NMR (CDCl3) δ1.27 (m, 12H), 1.53-1.63 (m, 4H), 2.26 (s, 3H), 2.54 (dd, 2H, J=7.6, 7.6 Hz), 3.31 (s, 3H), 3.46 (t, 2H, J=6.8 Hz), 4.57 (s, 2H), 4.69 (s, 2H), 5.19 (br s, 2H) and 7.35-7.37 (m, 5H); 13C NMR (CDCl3) δ 18.9, 26.2, 28.4, 29.36, 29.40, 29.5, 29.67, 29.70, 31.9, 55.0, 67.8, 75.9, 96.3, 127.9, 128.3, 128.3, 128.6, 128.6, 136.8, 142.8, 158.9, 161.1, 161.1 and 164.8; mass spectrum (APCI), m/z 416.2908 (M+H)+ (C24H38N3O3 requires 416.2913).

Provenance & Evidence