Dimethyl Sulfate → HCID 66926074, compound

HRID 2170804Notes

Reaction equation

HRID 2170804 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([CH:14]3[C:18](=[O:19])[CH2:17][CH2:16][C:15]3=[O:20])[C:11]([CH3:21])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:22](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]3[C:18](=[O:19])[CH2:17][CH2:16][C:15]=3[O:20][CH3:22])[C:11]([CH3:21])=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 669261742-[2-(4-Chloro-phenyl)-5-methyl-pyrimidin-4-yl]-cyclopentane-1,3-dione

Product 1

HCID 66926074HCID 66926074, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-[2-(4-Chloro-phenyl)-5-methyl-pyrimidin-4-yl]-cyclopentane-1,3-dione (650 mg, 2.16 mmol) was slurried in acetone (20 ml) and potassium carbonate (300 mg, 2.16 mmol) was added. After stirring at room temperature for 5 minutes, dimethyl sulphate (0.20 ml, 2.16 ml) was added in one portion and the reaction was heated to reflux. After 3 hours at reflux the reaction was complete and subsequently cooled to room temperature, before stripping to dryness. The resulting orange solid was re-solubilised in ethyl acetate (20 ml) and 1M sodium hydroxide (20 ml) and the biphasic mixture separated. The aqueous layer was further extracted with ethyl acetate (2×10 ml) before combining the organic layers, drying over magnesium sulphate, filtering and stripping to dryness to isolate a brown solid. This was purified by normal phase chromatography (gradient system of 100% dichloromethane−5% methanol:dichloromethane) to isolate 2-[2-(4-Chloro-phenyl)-5-methyl-pyrimidin-4-yl]-3-methoxy-cyclopent-2-enone as a yellow foam (526 mg, 1.67 mmol, 77% yield).

Workup

  1. temperaturethe reaction was heated to reflux
  2. temperatureAfter 3 hours at reflux the reaction
  3. temperaturesubsequently cooled to room temperature
  4. custom1M sodium hydroxide (20 ml) and the biphasic mixture separated
  5. extractionThe aqueous layer was further extracted with ethyl acetate (2×10 ml)
  6. dry with materialdrying over magnesium sulphate
  7. filtrationfiltering
  8. customto isolate a brown solid
  9. customThis was purified by normal phase chromatography (gradient system of 100% dichloromethane−5% methanol:dichloromethane)

Sources & evidence

ORD record
ord-fb7b2fbb0a424ad5a13ba044a4487386
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

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