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

HRID 55486Notes

Reaction equation

HRID 55486 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]2[C:6]([N:11]=1)=[N:7][CH:8]=[CH:9][CH:10]=2.[H-].[Na+].[CH3:14]I>CN(C)C=O>[OH:1][CH2:2][C:3]1[N:4]([CH3:14])[C:5]2[C:6]([N:11]=1)=[N:7][CH:8]=[CH:9][CH:10]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1282496(3H-imidazo(4,5-b)pyridin-2-yl)methanol

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-1H-imidazo[4,5-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-63b91ed0e8e4469f9996a933e45c1c30
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

Loading…