Potassium Carbonate → 2-(1-Methyl-3-trifluoromethylpyrazol-5-yl)-4-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-5-methylpyrimidine

HRID 1859397Notes

Reaction equation

HRID 1859397 reaction equation
I[C:2]1[N:7]=[CH:6][C:5]([CH3:8])=[C:4]([O:9][C:10]2[N:14]([CH3:15])[N:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:26][N:27]1[C:31](B(O)O)=[CH:30][C:29]([C:35]([F:38])([F:37])[F:36])=[N:28]1>C1(C)C=CC=CC=1.O.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:26][N:27]1[C:31]([C:2]2[N:3]=[C:4]([O:9][C:10]3[N:14]([CH3:15])[N:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=3)[C:5]([CH3:8])=[CH:6][N:7]=2)=[CH:30][C:29]([C:35]([F:38])([F:37])[F:36])=[N:28]1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 120567122-Iodo-6-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-5-methylpyrimidineHCID 120567131-Methyl-3-(trifluoroMethyl)pyrazole-5-boronic acid

Product 1

HCID 102947292-(1-Methyl-3-trifluoromethylpyrazol-5-yl)-4-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-5-methylpyrimidine

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 4A (1 g) in toluene (10 ml) is added a 2 M solution of potassium carbonate in water (2.5 ml) under an inert gas atmosphere. A suspension of 4B (0.66 g) and tetrakis(triphenylphosphine)palladium (0.15 g) in methanol (3 ml) is added and the mixture is heated to for 36 h to reflux. After cooling, the organic phase is separated and the water phase is washed twice with ethyl acetate. The combined organic phases are dried, evaporated to dryness and the residue is purified by silica-gel flash chromatography and preparative HPLC. One obtains the title compound as colorless crystals of mp. 113° C.

Workup

  1. additionis added
  2. temperaturethe mixture is heated to for 36 h
  3. temperatureto reflux
  4. temperatureAfter cooling
  5. customthe organic phase is separated
  6. washthe water phase is washed twice with ethyl acetate
  7. customThe combined organic phases are dried
  8. customevaporated to dryness
  9. customthe residue is purified by silica-gel flash chromatography and preparative HPLC

Sources & evidence

ORD record
ord-c2b9bf2052b244499804956fd1a7ec05
Source dataset
uspto-grants-2003_03
Patent number
US06528456B2

Reaction notes

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