Cesium carbonate → HCID 86685400, compound

HRID 570744Notes

Reaction equation

HRID 570744 reaction equation
C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.FC(F)(F)S(O[C:49]1[N:50]=[C:51]([CH2:68][CH2:69][C:70]([F:73])([F:72])[F:71])[N:52]([C:56]2[CH:61]=[CH:60][C:59]([O:62][CH2:63][C:64]([F:67])([F:66])[F:65])=[CH:58][CH:57]=2)[C:53](=[O:55])[CH:54]=1)(=O)=O.C1(C(C2C=CC=CC=2)=[NH:83])C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:83][C:49]1[N:50]=[C:51]([CH2:68][CH2:69][C:70]([F:72])([F:73])[F:71])[N:52]([C:56]2[CH:61]=[CH:60][C:59]([O:62][CH2:63][C:64]([F:65])([F:67])[F:66])=[CH:58][CH:57]=2)[C:53](=[O:55])[CH:54]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86685399HCID 86685399, compound

Product 1

HCID 86685400HCID 86685400, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tris(dibenzylideneacetone)dipalladium(0) (537 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (679 mg) in toluene (50 mL) were added 6-oxo-1-[4-(2,2,2-trifluoroethoxy)phenyl]-2-(3,3,3-trifluoropropyl)-1,6-dihydropyrimidin-4-yl trifluoromethanesulfonate (5.03 g), 1,1-diphenylmethanimine (1.97 mL) and cesium carbonate (7.97 g) at room temperature, and the mixture was stirred overnight at 100° C. The reaction mixture was concentrated under reduced pressure. To the residue was added THF, and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure. To a solution of the obtained residue in THF (100 mL) was added 1N hydrochloric acid (100 mL) at 0° C., and the mixture was stirred for 2 hr. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to aminopropylsilane-bonded silica gel column chromatography (ethyl acetate/hexane) and then silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.64 g) as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added THF
  3. customthe insoluble material was removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionTo a solution of the obtained residue in THF (100 mL) was added 1N hydrochloric acid (100 mL) at 0° C.
  6. stirringthe mixture was stirred for 2 hr
  7. extractionThe reaction mixture was extracted with ethyl acetate
  8. washthe extract was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12a396847e2e4b89b283aa5a1fd67812
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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