Water → 2-ethyl-5,7-dimethyl-3-(4-nitrobenzyl)-3H-imidazo[4,5-b]pyridine

Reaction equation

[CH2:1]([C:3]1[NH:13][C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].[OH2:14].[OH-:15].[Li+].O.C[N:19]([CH:21]=O)C>>[CH2:1]([C:3]1[N:13]([CH2:11][C:10]2[CH:9]=[CH:8][C:21]([N+:19]([O-:15])=[O:14])=[CH:6][CH:5]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

Reactant 4

HCID 962Water

HCID 6228Dimethylformamide

HCID 168937Lithium hydroxide, monohydrate

HCID 178437439HCID 178437439, compound

Product 1

HCID 104031282-ethyl-5,7-dimethyl-3-(4-nitrobenzyl)-3H-imidazo[4,5-b]pyridineYield 79.1%

Procedure

2-Ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine (U.S. Pat. No. 5,424,432) (3.50 g, 20.0 mmol) was dissolved in DMF (67 mL), and lithium hydroxide monohydrate (1.26 g, 30.0 mmol) was added thereto, followed by stirring at room temperature for 20 minutes. Then, p-nitorobenzylbromide (4.31 g, 20.0 mmol) was slowly added and stirred at room temperature for 30 minutes. Water (130 mL) was added to the reaction mixture and the precipitated crystals were collected by filtration, followed by washing with water. The crystals was dried under reduced pressure to obtain 2-ethyl-5,7-dimethyl-3-(4-nitrobenzyl)-3H-imidazo[4,5-b]pyridine (4.91 g, 15.8 mmol, yield 79.1%).