Potassium Carbonate → HCID 22610935, compound

HRID 843566Notes

Reaction equation

HRID 843566 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[NH:4][C:3]1=[O:13].C(=O)([O-])[O-].[K+].[K+].Cl[C:21]1[C:26]([F:27])=[CH:25][C:24]([C:28]#[N:29])=[C:23]([Cl:30])[N:22]=1>CS(C)=O.O>[F:27][C:26]1[C:21]([N:4]2[C:5](=[O:12])[CH:6]=[C:7]([C:8]([F:9])([F:11])[F:10])[N:2]([CH3:1])[C:3]2=[O:13])=[N:22][C:23]([Cl:30])=[C:24]([C:28]#[N:29])[CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 114354801-Methyl-6-trifluoromethylpyrimidine-2,4-dione

Product 1

HCID 22610935HCID 22610935, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 0.776 g 1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidin-dione, 0.760 g potassium carbonate and 0.768 g 2,6-dichloro-3-fluoro-5-cyanopyridin in 40 ml dimethylsulfoxide is stirred under nitrogen at 130° C. until conversion is complete. Then the reaction mixture is cooled down and diluted with ice and water. The pH of the mixture is adjusted to neutral and the mixture is extracted several times with ethyl acetate. The organic layers are washed with water, dried, evaporated and the residue is purified by silicagel chromatography (hexane/ethyl acetate 7/3) to yield the title compound as a solid of m.p. 146-148° C.

Workup

  1. temperatureThen the reaction mixture is cooled down
  2. extractionis extracted several times with ethyl acetate
  3. washThe organic layers are washed with water
  4. customdried
  5. customevaporated
  6. customthe residue is purified by silicagel chromatography (hexane/ethyl acetate 7/3)

Sources & evidence

ORD record
ord-885685c3d2d7477c923d6a70d67f563a
Source dataset
uspto-grants-2002_04
Patent number
US06380134B1

Reaction notes

Loading…