Dimethyl Sulfate → HCID 9847767, compound

HRID 1006227Notes

Reaction equation

HRID 1006227 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH:28]=[CH:29][C:30]=2[O:31][CH3:32])[O:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([N:19]3[C:24](=[O:25])[NH:23][C:22](=[O:26])[CH:21]=[N:20]3)=[CH:14][C:13]=2[CH3:27])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].[CH3:37]OS(OC)(=O)=O.C(OCC)(=O)C>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH:28]=[CH:29][C:30]=2[O:31][CH3:32])[O:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([N:19]3[C:24](=[O:25])[N:23]([CH3:37])[C:22](=[O:26])[CH:21]=[N:20]3)=[CH:14][C:13]=2[CH3:27])=[O:7])=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 22339706HCID 22339706, compound

Product 1

HCID 9847767HCID 9847767, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-{4-[3-(4-fluoro-benzoyl)-4-methoxy-phenoxy]-3,5-dimethyl-phenyl}-2H-[1,2,4]triazine-3,5-dione (50 mg) and potassium hydroxide (12 mg) in methanol (2 mL) was added dimethylsulfate (41 mg) to produce a thick slurry. After 3 h, the reaction mixture was diluted into ethyl acetate, washed with 1N aqueous sodium hydroxide, the organic layer dried over sodium sulfate, filtered and concentrated in vacuo. The resulting oil was flash chromatographed on silica gel (20%-35% ethyl acetate/hexanes) to afford the title compound of this EXAMPLE as a colorless solid, 24 mg. MS Calc.:475.5 Found:476.2 (M+1).

Workup

  1. customto produce a thick slurry
  2. washwashed with 1N aqueous sodium hydroxide
  3. dry with materialthe organic layer dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel (20%-35% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-06c9ebb586f34baab3a34e998c570a5c
Source dataset
uspto-grants-2004_09
Patent number
US06787652B1

Reaction notes

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