Hydrochloric Acid → HCID 12097346, compound

HRID 1354558Notes

Reaction equation

HRID 1354558 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[OH:22].Cl[CH:24]([C:29]([O:31][CH3:32])=[O:30])[C:25]([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:19])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[O:22][CH:24]([C:29]([O:31][CH3:32])=[O:30])[C:25]([O:27][CH3:28])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 120070Dimethyl chloromalonateHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 12097346HCID 12097346, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 20.0 g of 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenol, 10.8 g of dimethyl chloromalonate and 120 ml of N,N-dimethylformamide, 9.79 g of potassium carbonate were added and stirred at 70° C. for 1.5 hours. After the reaction mixture was cooled to room temperature, it was poured into a mixture of hydrochloric acid and ice and extracted with ethyl acetate. The organic layer was washed with 10% aqueous potassium carbonate solution and saturated brine subsequently, dried over anhydrous magnesium sulfate and concentrated. The residue was washed with methanol and diisopropyl ether to give 21.6 g of dimethyl [2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]malonate.

Workup

  1. additionwere added
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with 10% aqueous potassium carbonate solution and saturated brine subsequently
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. washThe residue was washed with methanol and diisopropyl ether

Sources & evidence

ORD record
ord-d1b73739460e4e08813cdc8d4503d899
Source dataset
uspto-grants-2007_05
Patent number
US07223862B2

Reaction notes

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