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

HRID 55488Notes

Reaction equation

HRID 55488 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]2[C:10]([N:11]=1)=[C:9]([CH3:12])[CH:8]=[CH:7][N:6]=2.[H-].[Na+].[CH3:15]I>CN(C)C=O>[CH3:15][N:4]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([CH3:12])=[C:10]2[N:11]=[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[5,4-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-4e1071a6a5994b2ebb89ff4df10d0fad
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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