Methyl iodide → 8-Benzyloxy-6-methoxymethyl-2,3-dimethylimidazo[1,2-a]pyridine

HRID 985106Notes

Reaction equation

HRID 985106 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:17]([CH3:21])=[C:18]([CH3:20])[N:19]=2)[CH:12]=[C:13]([CH2:15][OH:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24]I>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:17]([CH3:21])=[C:18]([CH3:20])[N:19]=2)[CH:12]=[C:13]([CH2:15][O:16][CH3:24])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 121060838-Benzyloxy-6-hydroxymethyl-2,3-dimethylimidazo[1,2-a]pyridine

Product 1

HCID 218739748-Benzyloxy-6-methoxymethyl-2,3-dimethylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.2 g of 8-benzyloxy-6-hydroxymethyl-2,3-dimethylimidazo[1,2-a]pyridine in 12 ml of dimethylformamide is treated with 0.36 g of 60% strength sodium hydride in paraffin under an inert gas atmosphere, stirred for 30 minutes at room temperature until the evolution of gas is complete, and then treated at room temperature with 0.56 ml of methyl iodide. After a reaction time of one hour, it is poured onto 100 ml of ice water and extracted 3 times with 100 ml of ethyl acetate each time. The organic phases are combined and washed with water. The solvent is stripped off in vacuo and the oily residue is chromatographed on silica gel (eluent: methylene chloride/methanol=100/1). 0.34 g of the title compound of melting point 107° C. (diethyl ether) is obtained.

Workup

  1. extractionextracted 3 times with 100 ml of ethyl acetate each time
  2. washwashed with water
  3. customthe oily residue is chromatographed on silica gel (eluent: methylene chloride/methanol=100/1)

Sources & evidence

ORD record
ord-6577fd01df164af1897572f9bdf9c8f6
Source dataset
uspto-grants-2005_03
Patent number
US06869949B2

Reaction notes

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