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

HRID 895665Notes

Reaction equation

HRID 895665 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]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 22380330Ethyl-2-(2-pyrimidin-2-yl-imidazol-1-ylmethyl)-1H-imidazo[4,5-c]pyridine

Product 1

HCID 223808165-benzyl-1-ethyl-2-(2-pyrimidin-2-yl-imidazol-1-ylmethyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridineYield 51%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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).

Workup

  1. temperatureis refluxed overnight
  2. temperatureto cool
  3. customThe solvent is decanted
  4. addition10 mL of MeOH is added to the residue
  5. customThe resultant solution is transferred to a 25 mL flask
  6. additionexcess NaBH4 is added to the solution
  7. additiontreated with 5 mL of 1 N HCl solution
  8. customevaporated
  9. extractionextracted with CH2Cl2
  10. extractionThe organic extract
  11. dry with materialis dried over Na2SO4
  12. filtrationfiltered
  13. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-03ebdcf03a00413a93b57666bac975f6
Source dataset
uspto-grants-2005_07
Patent number
US06916827B2

Reaction notes

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