Methyl Ethyl Ketone → HCID 22340997, compound

HRID 1166042Notes

Reaction equation

HRID 1166042 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([C:9]2[C:10](=[O:18])[N:11]([CH3:17])[C:12](=[S:16])[N:13]([CH3:15])[N:14]=2)=[C:4]([F:19])[CH:3]=1.Cl[C:21]1[N:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>CS(C)=O>[Cl:1][C:2]1[C:7]([O:8][C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:6][C:5]([C:9]2[C:10](=[O:18])[N:11]([CH3:17])[C:12](=[S:16])[N:13]([CH3:15])[N:14]=2)=[C:4]([F:19])[CH:3]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 22340990HCID 22340990, compound

Product 1

HCID 22340997HCID 22340997, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture 6-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4-dimethyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine (0.200 g), 2-chloropyrimidine (0.084 g), potassium carbonate (0.113 g), 2-butanone (10 ml), and dimethyl sulfoxide (2.5 ml) was heated at refluxed for 10 hours. The reaction was partitioned between water and ethyl acetate and the aqueous phase extracted with ethyl acetate (3×25 ml). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated to afford the desired material (0.21 g).

Workup

  1. temperatureat refluxed for 10 hours
  2. customThe reaction was partitioned between water and ethyl acetate
  3. extractionthe aqueous phase extracted with ethyl acetate (3×25 ml)
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bf75e83107034019bd1dc3f7d0fd164b
Source dataset
uspto-grants-2003_09
Patent number
US06613718B2

Reaction notes

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