Cesium carbonate → HCID 59362900, compound

HRID 1668823Notes

Reaction equation

HRID 1668823 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[C:21]4[CH2:22][CH2:23][CH2:24][C:20]=4[N:19]=[C:18](Cl)[N:17]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4].[NH:26]1[CH2:30][CH2:29][CH2:28][C:27]1=[O:31].C(=O)([O-])[O-].[Cs+].[Cs+]>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].O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[C:21]4[CH2:22][CH2:23][CH2:24][C:20]=4[N:19]=[C:18]([N:26]4[CH2:30][CH2:29][CH2:28][C:27]4=[O:31])[N:17]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 59362943HCID 59362943, compound

Product 1

HCID 59362900HCID 59362900, compoundYield 78%

Reagents, catalysts & solvents 2

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

Procedure

A glass tube was charged with 1-[4-(2-chloro-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid methyl ester (0.5 g, 1.4 mmol), 2-pyrrolidinone (0.17 g, 2 mmol) and alternatively purged and backfilled with nitrogen. Thereafter, tris(dibenzylideneacetone)dipalladium(0) (0.05 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthine (0.05 g), cesium carbonate (0.7 g, 2.2 mmol) and anhydrous 1,4-dioxane (6 mL) were introduced in the tube and again flushed with nitrogen. The reaction was stirred at a temperature in the range of 40° C. to 100° C. under stirring until complete as evidenced by the disappearance of starting chloro compound (TLC). The resulting mixture was cooled to a temperature in the range of 15° C. to 40° C., diluted with ethyl acetate (20 mL), filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford the title compound as a light yellow solid (0.44 g, 78% yield).

Workup

  1. customalternatively purged
  2. customagain flushed with nitrogen
  3. stirringunder stirring until complete
  4. temperatureThe resulting mixture was cooled to a temperature in the range of 15° C. to 40° C.
  5. additiondiluted with ethyl acetate (20 mL)
  6. filtrationfiltered through Celite
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-2ddea242e2404bea8a25a2b0fe56d855
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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