Tetrahydrofuran → 2,6-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-3-hydroxymethylimidazo[1,2-a]pyridine

HRID 1386068Notes

Reaction equation

HRID 1386068 reaction equation
[C:1]([C:6]1[N:10]2[CH:11]=[C:12]([CH3:26])[CH:13]=[C:14]([NH:15][CH2:16][C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:24][CH3:25])[C:9]2=[N:8][C:7]=1[CH3:27])(OCC)=[O:2].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH3:27][C:7]1[N:8]=[C:9]2[C:14]([NH:15][CH2:16][C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:24][CH3:25])=[CH:13][C:12]([CH3:26])=[CH:11][N:10]2[C:6]=1[CH2:1][OH:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 217173483-Carboethoxy-2,6-dimethyl-8-(2-ethyl-6-methylbenzylamino)imidazo[1,2-a]pyridine

Product 1

HCID 99963192,6-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-3-hydroxymethylimidazo[1,2-a]pyridineYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3-Carboethoxy-2,6-dimethyl-8-(2-ethyl-6-methylbenzylamino)imidazo[1,2-a]pyridine (1.0 g 2.8 mmol) was added to tetrahydrofuran (25 ml) and was stirred at +5° C. Lithium aluminum hydride (0.5 g, 13 mmol) was added in portions during 1.5 h so that the temperature remained below +10° C. After stirring the mixture at room temperature for an additional 1 h, 0.5 ml of water was added dropwise, followed by 0.5 ml of 15% sodium hydroxide and then 1.5 ml of water. The solids were removed by filtration and washed thoroughly with tetrahydrofuran and methylene chloride. The filtrate and washings were combined and dried and the solvents were removed under reduced pressure. The residue was solved in methylene chloride and washed with water. The organic layer was separated, dried over sodium sulfate, evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using ethylacetate:methylene chloride (1:1) as eluent. Crystallization from petroleum ether:diethyl ether (1:1) gave 0.37 g (41%) of the title compound.

Workup

  1. customremained below +10° C
  2. stirringAfter stirring the mixture at room temperature for an additional 1 h
  3. customThe solids were removed by filtration
  4. washwashed thoroughly with tetrahydrofuran and methylene chloride
  5. customdried
  6. customthe solvents were removed under reduced pressure
  7. washwashed with water
  8. customThe organic layer was separated
  9. dry with materialdried over sodium sulfate
  10. customevaporated under reduced pressure
  11. customthe residue was purified by column chromatography on silica gel
  12. customCrystallization from petroleum ether:diethyl ether (1:1)

Sources & evidence

ORD record
ord-ca0b6748b4be4c199b02245e714a2e0c
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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