Methanol → 5,6-Dihydro-4-methoxy-1-[[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]-2(1H)-pyridinone

HRID 2379144Notes

Reaction equation

HRID 2379144 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH2:10][CH2:9][NH:8][C:7](=[O:11])[CH:6]=1.Cl[CH2:13][C:14]1[N:15]=[CH:16][N:17]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]=1[CH3:19].CO>COCCOC>[CH3:3][O:4][C:5]1[CH2:10][CH2:9][N:8]([CH2:13][C:14]2[N:15]=[CH:16][N:17]([C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:18]=2[CH3:19])[C:7](=[O:11])[CH:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 110469654-(Chloromethyl)-5-methyl-1-trityl-1H-imidazoleHCID 136065754-methoxy-5,6-dihydro-2(1H)-pyridone

Product 1

HCID 104345435,6-Dihydro-4-methoxy-1-[[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]-2(1H)-pyridinoneYield 61.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

Sodium hydride (80% dispersion in oil; 360 mg) was suspended in dry DME (50 ml) under nitrogen and 5,6-dihydro-4-methoxy-2(1H)-pyridinone (1.27 g) in dry DME (20 ml) was added slowly. The resulting suspension was stirred at 20° for 1 h. 4-(Chloromethyl)-5-methyl-1-(triphenylmethyl)-1H-imidazole (3.72 g) in dry DME (50 ml) was added, and after the initial reaction had subsided the mixture was heated to 50° for 4 h and then cooled. Methanol (5 ml) was added dropwise, and solvent was removed invacuo. 8% Aqueous sodium bicarbonate solution (300 ml) was added to the residue and the resulting solution was extracted with dichloromethane (2×300 ml), dried and evaporated in vacuo to leave an oil which was purified by FCC eluting with System A (200:8:1) to give the title compound (2.84 g), m.p. 181°-184°.

Workup

  1. customafter the initial reaction
  2. temperaturewas heated to 50° for 4 h
  3. temperaturecooled
  4. customsolvent was removed invacuo
  5. addition8% Aqueous sodium bicarbonate solution (300 ml) was added to the residue
  6. extractionthe resulting solution was extracted with dichloromethane (2×300 ml)
  7. customdried
  8. customevaporated in vacuo
  9. customto leave an oil which
  10. customwas purified by FCC
  11. washeluting with System A (200:8:1)

Sources & evidence

ORD record
ord-fff725d6ee724462a53a1784e51845ee
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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