Methyl iodide → 5-Chloro-2-hydroxymethyl-3-methylimidazo[5,4-b]pyridine

HRID 1601818Notes

Reaction equation

HRID 1601818 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][C:9]([CH2:11][OH:12])=[N:10][C:5]2=[CH:4][CH:3]=1.[H-].[Na+].[CH3:15]I>CN(C)C=O>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:15])[C:9]([CH2:11][OH:12])=[N:10][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178519929HCID 178519929, compound

Product 1

HCID 106555445-Chloro-2-hydroxymethyl-3-methylimidazo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 15 was repeated, except that 3.00 g of 5-chloro-2-hydroxymethyl-3H-imidazo[4,5-b]pyridine (prepared as described in Preparation 43), 0.71 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 1.1 ml of methyl iodide and 70 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 1.60 g of the title compound, melting at 204-210° C.

Workup

  1. customA procedure similar to that described in Preparation 15

Sources & evidence

ORD record
ord-75e57588984840ab8641cca8ee6a5357
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Reaction notes

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