8-Benzyloxy-6-methoxymethyl-2,3-dimethylimidazo[1,2-a]pyridine → 6-Methoxymethyl-2,3-dimethyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-8-one

HRID 723407Notes

Reaction equation

HRID 723407 reaction equation
C([O:8][C:9]1[C:10]2[N:11]([C:18]([CH3:22])=[C:19]([CH3:21])[N:20]=2)[CH:12]=[C:13]([CH2:15][O:16][CH3:17])[CH:14]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:17][O:16][CH2:15][CH:13]1[CH2:12][N:11]2[C:18]([CH3:22])=[C:19]([CH3:21])[N:20]=[C:10]2[C:9](=[O:8])[CH2:14]1

Participants

5

Reactant 2

HCID 218739748-Benzyloxy-6-methoxymethyl-2,3-dimethylimidazo[1,2-a]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 218739786-Methoxymethyl-2,3-dimethyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-8-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

19.2 g of 8-benzyloxy-6-methoxymethyl-2,3-dimethylimidazo[1,2-a]pyridine, dissolved in 100 ml of methanol, are treated with 1.9 g of palladium (10% strength on activated carbon, Merck) and hydrogenated with hydrogen at 80° C. using a pressure of 50 bar. After absorption of hydrogen is complete, the catalyst is filtered off, washed with methanol and methylene chloride and the combined filtrate is concentrated to dryness in vacuo. After purification on silica gel (eluent: methylene chloride/methanol=13/1), 7.6 g of the title compound of melting point 103–104° C. are obtained.

Workup

  1. customAfter absorption of hydrogen
  2. filtrationthe catalyst is filtered off
  3. washwashed with methanol and methylene chloride
  4. concentrationthe combined filtrate is concentrated to dryness in vacuo
  5. customAfter purification on silica gel (eluent: methylene chloride/methanol=13/1), 7.6 g of the title compound of melting point 103–104° C.
  6. customare obtained

Sources & evidence

ORD record
ord-3bec044814bf4aed92d7ced921bc0de9
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

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