Methyl iodide → 6-Chloro-2-hydroxymethyl-3-methylimidazo[4,5-b]pyridine

HRID 1953717Notes

Reaction equation

HRID 1953717 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][OH:12])[NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:15]I>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][OH:12])[N:8]([CH3:15])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178519935HCID 178519935, compound

Product 1

HCID 106317996-Chloro-2-hydroxymethyl-3-methylimidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 59 was repeated, except that 3.00 g of 6-chloro-2 -hydroxymethyl-3H-imidazo[5,4-b]pyridine (prepared as described in Preparation 63), 0.71 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 1.03 ml of methyl iodide and 50 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 50:1 by volume as the eluent, to give 0.87 g of the title compound, melting at 141-142° C.

Workup

  1. customA procedure similar to that described in Preparation 59

Sources & evidence

ORD record
ord-1533ebd64ed84d6e8754067b69755499
Source dataset
uspto-grants-2000_09
Patent number
US06117893

Reaction notes

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