Water → HCID 21310545, compound

HRID 583123Notes

Reaction equation

HRID 583123 reaction equation
[H-].[Na+].[I-].C[S+](C)(C)=O.O=[C:10]1[CH2:15][CH2:14][CH:13]([N:16]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH3:28])[N:22]=3)=[C:19]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[N:18]=[CH:17]2)[CH2:12][CH2:11]1.O.[CH2:37]1[CH2:41][O:40]CC1>CS(C)=O>[O:40]1[CH2:41][CH:37]1[CH:10]1[CH2:11][CH2:12][CH:13]([N:16]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH3:28])[N:22]=3)=[C:19]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[N:18]=[CH:17]2)[CH2:14][CH2:15]1

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 10090302HCID 10090302, compound

Product 1

HCID 21310545HCID 21310545, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Added to a mixture of sodium hydride (0.05 g, 0.88 mmol) in DMSO (1 mL) was trimethyl sulfoxonium iodide (0.29 g, 1.3 mmol). After stirring the resultant mixture 1.5 h. (when gas evolution ceases), 1-(4-oxocyclohexyl)-4-(4-fluorophenyl)-5-[(2-methoxy)pyrimidin-4-yl]imidazole from example 1(j) (0.322 g, 0.88 mmol) suspended in dry THF (4 mL) was added and the mixture was stirred 4 h. The mixture was poured into H2O and extracted with EtOAc. The organic phase was dried (Na2SO4) and concentrated. The resulting residue was suspended in EtOAc/hexane (1:1) and filtered. The solid was purified by flash chromatography (silica gel 2% MeOH/CH2Cl2) to afford the title compound as white crystals (0.18 g, 53% yield) 1H NMR (CDCl3): δ 8.35 (d, 1H), 7.85 (s, 1H), 7.43 (q, 2H), 7.02 (t, 2H), 6.80 (d, 1H), 4.86 (m, 1H), 4.09 (s, 3H), 2.76 (s, 2H), 226 (m, 2H), 2.20-2.02 (m, 4H), 1.43 (d, 2H).

Workup

  1. additionwas added
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated
  5. filtrationfiltered
  6. customThe solid was purified by flash chromatography (silica gel 2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-023d925c6c3046ad99e777b80bff3782
Source dataset
uspto-grants-1999_07
Patent number
US05929076

Reaction notes

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