Methyl iodide → 2-(3-Hydroxypropyl)-3-methylimidazo[5,4-b]pyridine

HRID 356281Notes

Reaction equation

HRID 356281 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[NH:6][C:7]2[C:12]([N:13]=1)=[CH:11][CH:10]=[CH:9][N:8]=2.[H-].[Na+].[CH3:16]I>CN(C)C=O>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[N:6]([CH3:16])[C:7]2[C:12]([N:13]=1)=[CH:11][CH:10]=[CH:9][N:8]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178520526HCID 178520526, compound

Product 1

HCID 105838782-(3-Hydroxypropyl)-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 3.40 g of 2-(3-hydroxy-propyl)-3H-imidazo[5,4-b]pyridine (prepared as described in Preparation 33), 0.81 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 1.2 ml of methyl iodide and 100 ml of dimethylformamide were used, to give the title compound as a crude product. This crude product was purified by column chromatograpy through silica gel, using a 10:1 by volume mixture of ethyl acetate and methanol as the eluent. The product was crystallized by trituration with ethyl acetate, to give 3.10 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-a4335520b05e41aea4265e933128d2c2
Source dataset
uspto-grants-1998_11
Patent number
US05834501

Reaction notes

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