Methanol → 8-(2,6-Dimethylbenzylamino)-2-methoxymethyl-3-methyl-imidazo[1,2-a]pyridine

HRID 1006671Notes

Reaction equation

HRID 1006671 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]2[C:10]([NH:11][CH2:12][C:13]3[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:20])=[CH:9][CH:8]=[CH:7][N:6]2[C:21]=1[CH3:22].[CH3:23][OH:24]>>[CH3:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:13]=1[CH2:12][NH:11][C:10]1[C:5]2[N:6]([C:21]([CH3:22])=[C:3]([CH2:2][O:24][CH3:23])[N:4]=2)[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 226726282-Chloromethyl-8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine

Product 1

HCID 185164128-(2,6-Dimethylbenzylamino)-2-methoxymethyl-3-methyl-imidazo[1,2-a]pyridineYield 44%

Procedure

2-chloromethyl-8-(2,6-dimethylbenzylamino)-3-methylimidazo[1,2-a]pyridine (0.3 g, 0.96 mmol) was solved in methanol (20 ml) and stirred for 20 h. at room temperature and refluxed for 20 min. The solvent was evaporated under reduced pressure and the residue was dissolved in methylene chloride and washed with a bicarbonate solution. The organic layer was separated, dried (Na2SO4) and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using diethyl ether:petroleum ether (2:1) as eluent and crystallization from diethyl ether:petroleum ether (2:1) gave 0.13 g (44%) of the desired product.

Workup

  1. temperaturerefluxed for 20 min
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed with a bicarbonate solution
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customPurification of the residue by column chromatography on silica gel
  9. customcrystallization from diethyl ether:petroleum ether (2:1)

Sources & evidence

ORD record
ord-5c917d510df340b39d88ede126819282
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

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