Potassium Phosphate, Tribasic → HCID 21025895, compound

HRID 714647Notes

Reaction equation

HRID 714647 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([F:21])([F:20])[F:9])[N:7]=1

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 116296072-Chloro-4-methylpyrimidine

Product 1

HCID 21025895HCID 21025895, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Under an atmosphere of argon, 250 mg (1.95 mmol) of 2-chloro-4-methylpyrimidine and 583 mg (2.92 mmol) of 2-(trifluoromethyl)phenylboronic acid were dissolved in 8 ml of toluene. 89 mg (0.10 mmol) of tris(dibenzylideneacetone)dipalladium, 77 mg (0.19 mmol) of 2-dicyclohexyl-phosphino-2′-(N,N-dimethylamino)biphenyl and 826 mg (3.89 mmol) of potassium phosphate were then added, and under argon the mixture was heated at 110° C. for 20 h. For work-up, the mixture was diluted at RT with 15 ml of ethyl acetate and 15 ml of water, the organic phase was separated off and the aqueous phase extracted two more times with in each case 15 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1, then 4:1). This gave 249 mg (54% of theory) of the target compound in a purity of 87%.

Workup

  1. customthe organic phase was separated off
  2. extractionthe aqueous phase extracted two more times with in each case 15 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified chromatographically on silica gel (mobile phase

Sources & evidence

ORD record
ord-485f8b57c393485797995aeef23feb85
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

Loading…