Methyl iodide → 8-Benzyloxy-6-methoxymethyl-2,3-dimethylimidazo[1,2-a]pyridine
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]=1Participants
Procedure
Under an atmosphere of inert gas, a suspension of 1.2 g of 8-benzyloxy-6-hydroxymethyl-2,3-dimethylimidazo[1,2-a]pyridine in 12 ml of dimethylformamide is admixed with 0.36 g of 60% sodium hydride in paraffin, and the mixture is stirred at room temperature for 30 minutes, until the generation of gas has ceased, and then, at room temperature, admixed with 0.56 ml of methyl iodide. After a reaction time of one hour, the mixture is poured into 100 ml of ice-water and extracted three times with in each case 100 ml of ethyl acetate. The organic phases are combined and washed with water. The solvent is removed in vacuo and the oily residue is chromatographed on silica gel (mobile phase: methylene chloridelmethanol=100/1). This gives 0.34 g of the title compound of melting point 107° C. (diethyl ether).
Workup
- customat room temperature
- extractionextracted three times with in each case 100 ml of ethyl acetate
- washwashed with water
- customThe solvent is removed in vacuo
- customthe oily residue is chromatographed on silica gel (mobile phase: methylene chloridelmethanol=100/1)
Sources & evidence
- ORD record
- ord-81c653e2550948a39c9d0abcfd4ccad9
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06696461B2
Reaction notes
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