Benzyl Bromide → 5-benzyl-1-ethyl-2-(2-pyrimidin-2-yl-imidazol-1-ylmethyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine
Reaction equation
[CH2:1]([N:3]1[C:11]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[N:5]=[C:4]1[CH2:12][N:13]1[CH:17]=[CH:16][N:15]=[C:14]1[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH3:2].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(C)=O>[CH2:24]([N:8]1[CH2:9][CH2:10][C:11]2[N:3]([CH2:1][CH3:2])[C:4]([CH2:12][N:13]3[CH:17]=[CH:16][N:15]=[C:14]3[C:18]3[N:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:5][C:6]=2[CH2:7]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1-ethyl-2-(2-pyrimidin-2-yl-imidazol-1-ylmethyl)-1H-imidazo[4,5-c]pyridine (100 mg, prepared as described in Example 2) and benzyl bromide (42 mg) in 5 mL of acetone in a sealed tube is refluxed overnight and then allowed to cool. The solvent is decanted and 10 mL of MeOH is added to the residue. The resultant solution is transferred to a 25 mL flask, excess NaBH4 is added to the solution. The reaction mixture is then stirred at room temperature for about one hour, treated with 5 mL of 1 N HCl solution and evaporated. The residue is made basic with 1N NaOH solution and extracted with CH2Cl2. The organic extract is dried over Na2SO4, filtered and the solvents removed under reduced pressure. Column chromatography of the residue on silica gel (10% MeOH in CH2Cl2 as eluent) gives 5-benzyl-1-ethyl-2-(2-pyrimidin-2-yl-imidazol-1-ylmethyl)-4,5,6,7-tetrahydro-1H -imidazo[4,5-c]pyridine (50 mg). 1H NMR (CDCl3): 8.85 (d, 1H), 7.20-7.40 (m, 8H), 7.10 (s, H), 6.05(s, 2H), 3.80 (q, 2H), 3.70 (s, 2H), 3,55(s, 2H), 2.78(t, 2H), 2.58 (t, 2H), 0.96 (t, 3H).