Potassium Carbonate → HCID 11177155, compound

HRID 1953966Notes

Reaction equation

HRID 1953966 reaction equation
O[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([F:10])([F:9])[F:8].Cl[C:12]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[N:15]=[C:14]([CH3:28])[CH:13]=1.C([O-])([O-])=[O:30].[K+].[K+]>CN(C)C=O.O>[CH3:28][C:14]1[CH:13]=[C:12]([O:30][C:6]2[CH:2]=[C:3]([C:7]([F:10])([F:9])[F:8])[S:4][CH:5]=2)[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[N:15]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 113463254-chloro-6-methyl-2-[4-(trifluoromethyl)phenyl]pyrimidineHCID 23295691HCID 23295691, compound

Product 1

HCID 11177155HCID 11177155, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-hydroxy-2-(trifluoromethyl)thiophene (0.50 g, 2.98 mmol) and 6-chloro-4-methyl-2-(α,α,α-trifluoro-p-tolyl)pyrimidine (0.31g, 2.98 mmol) in dimethylformamide is treated with K2CO3 (0.62 g, 4.47 mmol), heated at 100° C. for 17 hours, cooled to room temperature and diluted with water. The resultant reaction mixture is extracted with ether. The ether extracts are combined, washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to give a brown solid residue. The residue is chromatographed (silica gel, ethyl acetate/hexanes, 20/80) to give the title product as a light yellow solid, 0.88 g (73% yield), mp 83.5-85° C., identified by 1HNMR, 13CNMR, 19FNMR, mass spectral and elemental analyses.

Workup

  1. temperaturecooled to room temperature
  2. customThe resultant reaction mixture
  3. extractionis extracted with ether
  4. washwashed sequentially with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a brown solid residue
  8. customThe residue is chromatographed (silica gel, ethyl acetate/hexanes, 20/80)

Sources & evidence

ORD record
ord-aa107e36ce244ca881a0ed80e1612e47
Source dataset
uspto-grants-2000_09
Patent number
US06121202

Reaction notes

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