Dimethyl Sulfate → 3-(5-acetylamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 380799Notes

Reaction equation

HRID 380799 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[NH:15][C:14]2=[O:24])=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6].[C:25](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>O1CCCC1.O.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[N:15]([CH3:25])[C:14]2=[O:24])=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6]

Participants

7

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 183658882'-chloro-5'-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4'-fluoroacetanilide

Product 1

HCID 183659043-(5-acetylamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedioneYield 85.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2′-chloro-5′-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4′-fluoroacetanilide (0.85 g, 2.3 mmol), potassium carbonate (0.32 g, 2.3 mmol) and dimethylsulfate (0.22 mL, 2.3 mmol) in tetrahydrofuran is refluxed for 90 minutes, cooled to room temperature, and diluted with water and chloroform. The resultant mixture is concentrated in vacuo to obtain an aqueous suspension which is filtered to give the title product as an off-white solid (0.75 g, mp 257-258.5° C.).

Workup

  1. temperatureis refluxed for 90 minutes
  2. concentrationThe resultant mixture is concentrated in vacuo
  3. customto obtain an aqueous suspension which
  4. filtrationis filtered

Sources & evidence

ORD record
ord-9c5844fdcb744982acb6b11e4cf3cca7
Source dataset
uspto-grants-2001_10
Patent number
US06303783B1

Reaction notes

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