Hydroxyamine hydrochloride → HCID 67328311, compound

Reaction equation

CC1[N:3]([C:8]2[N:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:10]([CH3:23])[N:9]=2)C(C)=CC=1.Cl.NO>C(O)C.O.O>[NH2:3][C:8]1[N:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:10]([CH3:23])[N:9]=1

Participants

Procedure

To a stirred solution containing 2.85 g (9.27 mmol) 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-benzyloxy-4,6-dimethylpyrimidine (6) in 30 mL of ethanol-water 1:1 were added 6.44 g (93 mmol) of hydroxylamine hydrochloride. The reaction mixture was stirred at reflux overnight under argon atmosphere. The pH of the solution was then brought to 10 and diluted with 20 mL of water. The mixture was extracted with two portions of 30 mL of dichloromethane. The combined organic solution was dried (MgSO4) and then concentrate under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with acetone-hexanes 1:2 gave the expected product as white solid. Yield: 2.1 g (98%). 1H-NMR (CDCl3) δ 7.39 (m, 5H), 4.80 (br. 2H), 4.74 (s, 2H), 2.29 (s, 6H). 13C-NMR (CDCl3) 160.05, 158.45, 141.50, 137.02, 37.27, 19.22.