Methyl iodide → 3,7-Dimethyl-2-hydroxymethylimidazo[4,5-b]pyridine

HRID 1601815Notes

Reaction equation

HRID 1601815 reaction equation
[OH:1][CH2:2][C:3]1[NH:12][C:6]2=[N:7][CH:8]=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1.[H-].[Na+].[CH3:15]I>CN(C)C=O>[CH3:15][N:12]1[C:6]2=[N:7][CH:8]=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=[C:3]1[CH2:2][OH:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178428359HCID 178428359, compound

Product 1

HCID 107736513,7-Dimethyl-2-hydroxymethylimidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 15 was repeated, except that 5.00 g of 2-hydroxymethyl-7-methyl-3H-imidazo[4,5-b]pyridine, 1.34 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 2.0 ml of methyl iodide and 120 ml of dimethylformamide were used, to give the title compound as a crude product. This crude product was purified by column chromatography through silica gel, using a gradient elution method, with mixtures of ethyl acetate and methanol in ratios ranging from 1:0 to 10:1 by volume as the eluent, to give 4.4 g of the title compound, melting at >300° C.

Workup

  1. customA procedure similar to that described in Preparation 15

Sources & evidence

ORD record
ord-2241e6992f8846f3b9aa9612d1a19cf8
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Reaction notes

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