Methyl iodide → HCID 21994459, compound

HRID 1977613Notes

Reaction equation

HRID 1977613 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:21])[NH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:13][CH:14]=1.CI.[C:24](=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:21])[N:11]([CH3:24])[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:13][CH:14]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21994460HCID 21994460, compound

Product 1

HCID 21994459HCID 21994459, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 5-(2-methoxyphenyl)-2-phenyl-3H-pyrimidin-4-one (0.4 g, example 9), methyl iodide (0.134 ml), potassium carbonate (0.398 g) and tetrabutylammonium bromide (0.048 g) in toluene (60 ml) and water (10 ml) was refluxed for 2 hours and then evaporated. The residue was taken up in diethyl ether and insolubles were filtered off. The ether solution was evaporated, and the residue was purified by flash chromatography on silica gel (eluent: n-hexane/ethyl acetate 6:4), to give the title compound in a pure form as a white solid (0.22 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customevaporated
  3. filtrationinsolubles were filtered off
  4. customThe ether solution was evaporated
  5. customthe residue was purified by flash chromatography on silica gel (eluent: n-hexane/ethyl acetate 6:4)

Sources & evidence

ORD record
ord-573c5f5cf97c4f629639e9aedbdd6934
Source dataset
uspto-grants-2001_05
Patent number
US06235738B1

Reaction notes

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