Methyl iodide → 2-t-Butyldimethylsilyloxymethyl-1-methylimidazo[4,5-c]pyridine

HRID 55516Notes

Reaction equation

HRID 55516 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[CH3:21]I>CN(C)C=O>[Si:1]([O:8][CH2:9][C:10]1[N:11]([CH3:21])[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178455180HCID 178455180, compound

Product 1

HCID 232983402-t-Butyldimethylsilyloxymethyl-1-methylimidazo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 59 was repeated, except that 7.4 g of 2-t-butyldimethylsilyloxymethyl-1H-imidazo[4,5-c]pyridine (prepared as described in Preparation 71), 1.23 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 2.0 ml of methyl iodide and 200 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 10:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 3.30 g of the title compound, melting at 93°-95° C.

Workup

  1. customA procedure similar to that described in Preparation 59

Sources & evidence

ORD record
ord-dacb15cab1c34cc5a15c177af5173843
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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