Water → 8-(2,6-Dimethylbenzylamino)-2-hydroxymethyl-3-methylimidazo[1,2-a]pyridine

HRID 1166159Notes

Reaction equation

HRID 1166159 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH3:20])=[C:13]([C:15](OCC)=[O:16])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH3:20])=[C:13]([CH2:15][OH:16])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22672581Ethyl 8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 98826348-(2,6-Dimethylbenzylamino)-2-hydroxymethyl-3-methylimidazo[1,2-a]pyridineYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridin-2-carboxylate (5.2 g, 0.015 mol) was solved in tetrahydrofuran (100 ml) and LiAlH4 (1.15 g 0.03 mol) was added. After stirring the mixture at room temperature for 45 min, 1.15 ml of water was added dropwise, followed by 1.15 ml of 15% sodium hydroxide and then 3.45 ml of water. The solids were removed by filtration and washed thoroughly with methylene chloride. The filtrate and washings were combined and dried and the solvents were removed under reduced-pressure. Purification of the residue by column chromatography on silica gel using methylene chloride : methanol (10:2) as eluent gave 3.2 g (73%) of the title compound.

Workup

  1. customThe solids were removed by filtration
  2. washwashed thoroughly with methylene chloride
  3. customdried
  4. customthe solvents were removed under reduced-pressure
  5. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-1324ae05e2c843799d6542040ddbd067
Source dataset
uspto-grants-2003_09
Patent number
US06613775B1

Reaction notes

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