Methyl iodide → 2-Hydroxymethyl3,5,7-trimethylimidazo[5,4-b]pyridine

HRID 55528Notes

Reaction equation

HRID 55528 reaction equation
[OH:1][CH2:2][C:3]1[NH:13][C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1.[H-].[Na+].I[CH3:17]>CN(C)C=O>[OH:1][CH2:2][C:3]1[N:13]([CH3:17])[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178423977HCID 178423977, compound

Product 1

HCID 107263792-Hydroxymethyl3,5,7-trimethylimidazo[5,4-b]pyridineYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 15 was repeated, except that 2.6 g of 2-hydroxymethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine (prepared as described in Preparation 85), 0.64 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 2.2 g of iodomethane and 80 ml of dimethylformamide were used. After working up the product as described in Preparation 15, the resulting crude product was purified by column chromatography through silica gel, using a 1:6 by volume mixture of ethanol and ethyl acetate as the eluent, followed by recrystallization from ethyl acetate, to give 1.5 g of the title compound, melting at 178°-179° C.

Workup

  1. customA procedure similar to that described in Preparation 15
  2. customas described in Preparation 15
  3. customthe resulting crude product was purified by column chromatography through silica gel
  4. additionby volume mixture of ethanol and ethyl acetate as the eluent
  5. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-6bee7e6a0dbe41d78c2171dc7a2b64a8
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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