Potassium Hydroxide → HCID 67327945, compound

Participants

Reaction Steps

To stirred solution containing 343 mg (0.63 mmol) of 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-benzyloxy-4-methyl-6-(10-benzyloxydecyl)-pyrimidine (7) in 10 mL of ethanol-water 9:1 were added 500 mg (7.19 mmol) of hydroxylamine hydrochloride followed by 400 mg (7.14 mmol) of potassium hydroxide. The reaction mixture was then stirred at reflux under argon atmosphere overnight. A second portion of 500 mg (7.19 mmol) of hydroxylamine hydrochloride was added and the reaction mixture was stirred overnight at reflux under argon atmosphere. The reaction mixture was then poured into 70 mL of water and then basified to a pH 9-10 with a 1N NaOH solution. The mixture was extracted with two portions of 70 mL of dichloromethane. The combined organic solution was washed with a portion of 70 mL of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with acetone-hexanes 2:1 gave the expected product as a colorless oil: yield 153 mg (52%). 1H-NMR (CDCl3) δ 7.48-7.37 (m, 10H), 5.17 (br., 2H), 4.69 (s, 2H), 4.45 (s, 2H), 3.41 (t, 2H, J=6.8), 2.55 (t, 2H, J=7.6), 2.26 (s, 3H), 1.63-1.53 (m, 4H), 1.27 (m, 12H); 13C-NMR (CDCl3) δ 164.85, 161.14, 158.88, 142.81, 138.71, 136.77, 129.16, 128.59, 128.26, 75.91, 72.83, 70.50, 31.90, 29.77, 29.22, 29.55, 29.45, 29.41, 28.44, 28.19, 19.00.

Provenance & Evidence