Cesium carbonate → HCID 59558786, compound

HRID 2388811Notes

Reaction equation

HRID 2388811 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:13]1[CH:18]=[C:17]([S:19][CH3:20])[N:16]=[C:15]([S:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=2[F:30])[N:14]=1.[Cl-].[NH4+]>O1CCOCC1.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]>[F:30][C:24]1[C:25]([F:29])=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][S:21][C:15]1[N:14]=[C:13]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:18]=[C:17]([S:19][CH3:20])[N:16]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 72879MethanesulfonamideHCID 86619883HCID 86619883, compound

Product 1

HCID 59558786HCID 59558786, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methane sulfonamide (0.22 g), tris(dibenzylideneacetone)-dipalladium (0) (33 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl(XPHOS) (17 mg), cesium carbonate (0.58 g) and 4-chloro-2-[(2,3-difluorobenzyl)thio]-6-(methylthio)pyrimidine (the product of step i) (0.38 g) in dioxane (10 mL) was heated at 100° C. for 18 h. The mixture was cooled and saturated ammonium chloride was added and the resulting mixture extracted with EtOAc. The combined organic extracts were washed with saturated aqueous sodium chloride, dried (MgSO4), filtered and evaporated. The residue was purified by reverse phase HPLC eluting with acetonitrile/aq. 0.1% TFA mixtures to give the title compound as a white solid. Yield: 30 mg.

Workup

  1. temperatureThe mixture was cooled
  2. extractionthe resulting mixture extracted with EtOAc
  3. washThe combined organic extracts were washed with saturated aqueous sodium chloride
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by reverse phase HPLC
  8. washeluting with acetonitrile/aq

Sources & evidence

ORD record
ord-a25748a8bbb54208b12db8b7db99cb1d
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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