Methyl iodide → HCID 11302500, compound

HRID 1725572Notes

Reaction equation

HRID 1725572 reaction equation
[CH2:1]([C:3]1[C:4](=[O:25])[N:5]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])=[N:7][C:8]=1[CH3:9])[CH3:2].[C:26](=O)([O-])[O-].[K+].[K+].IC>C1COCC1>[CH2:1]([C:3]1[C:4](=[O:25])[N:5]([CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:26])=[N:7][C:8]=1[CH3:9])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135454814HCID 135454814, compound

Product 1

HCID 11302500HCID 11302500, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-ethyl-2-(2-hydroxy-phenyl)-6-methyl-3-phenethyl-3H-pyrimidin-4-one (0.19 g, 0.50 mmol) was dissolved in THF (10 mL) that contained potassium carbonate (0.80 g) and iodomethane (3 mL). The mixture was refluxed for 40 h under an argon atmosphere. After cooling to room temperature, hexanes (100 mL) were added and the salts were filtered off. The filtrate was evaporated in vacuum, and the residue was purified by flash chromatography on silica gel (40 g) eluting with ethyl acetate-hexanes (2:3) to give 5-ethyl-2-(2-methoxy-phenyl)-6-methyl-3-phenethyl-3H-pyrimidin-4-one (110 mg, 56%) as a white solid after final crystallization from hexanes.

Workup

  1. temperatureThe mixture was refluxed for 40 h under an argon atmosphere
  2. filtrationthe salts were filtered off
  3. customThe filtrate was evaporated in vacuum
  4. customthe residue was purified by flash chromatography on silica gel (40 g)
  5. washeluting with ethyl acetate-hexanes (2:3)

Sources & evidence

ORD record
ord-7d104be3f4da4e11a03774a882f5fb44
Source dataset
uspto-grants-2009_02
Patent number
US07491728B2

Reaction notes

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