Methyl iodide → (1-methyl-1H-imidazo[4,5-b]pyridin-2-yl)methanol

HRID 356279Notes

Reaction equation

HRID 356279 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][N:6]=2.[H-].[Na+].[CH3:14]I>CN(C)C=O>[OH:1][CH2:2][C:3]1[N:11]([CH3:14])[C:10]2[C:5]([N:4]=1)=[N:6][CH:7]=[CH:8][CH:9]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178519938HCID 178519938, compound

Product 1

HCID 10749525(1-methyl-1H-imidazo[4,5-b]pyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 15 was repeated, except that 45 g of 2-hydroxymethyl-3H-imidazo[5,4-b]pyridine, 13.17 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 20.7 ml of methyl iodide and 1.43 liter 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 1:1 by volume as the eluent, to give 3.24 g of the title compound, melting at 130°-132° C.

Workup

  1. customA procedure similar to that described in Preparation 15

Sources & evidence

ORD record
ord-2829ffab7f5f472a889c1163eaa4755e
Source dataset
uspto-grants-1998_11
Patent number
US05834501

Reaction notes

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