Cesium carbonate → HCID 86685402, compound

HRID 570747Notes

Reaction equation

HRID 570747 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][CH3:70])[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.[CH3:73][O:74][C:75]1[CH:82]=[CH:81][C:78]([CH2:79][NH2:80])=[CH:77][CH:76]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(OCC)(=O)C>[CH3:73][O:74][C:75]1[CH:82]=[CH:81][C:78]([CH2:79][NH:80][C:49]2[N:50]=[C:51]([CH2:68][CH2:69][CH3:70])[N:52]([C:56]3[CH:57]=[CH:58][C:59]([O:62][CH2:63][C:64]([F:66])([F:67])[F:65])=[CH:60][CH:61]=3)[C:53](=[O:55])[CH:54]=2)=[CH:77][CH:76]=1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 754524-MethoxybenzylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86685403HCID 86685403, compound

Product 1

HCID 86685402HCID 86685402, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of palladium(II) acetate (49.0 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (189 mg) in toluene (20 mL) were added 6-oxo-2-propyl-1-[4-(2,2,2-trifluoroethoxy)phenyl]-1,6-dihydropyrimidin-4-yl trifluoromethanesulfonate (1.0 g), 4-methoxybenzylamine (0.43 mL) and cesium carbonate (1.77 g) at room temperature, and the mixture was stirred at 100° C. for 3 hr. To the reaction mixture were added ethyl acetate and water, and the mixture was extracted with ethyl acetate. 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) to give the title compound (462 mg) as a solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-63c14c37174d4f1a8ea66f0eeea8147e
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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