Cesium carbonate → HCID 58635320, compound

HRID 1827246Notes

Reaction equation

HRID 1827246 reaction equation
FC(F)(F)C(O)=O.[C:8]1([C@@H:14]2[CH2:16][C@H:15]2[C:17]([N:19]2[CH2:24][CH2:23][CH:22]([CH2:25][NH2:26])[CH2:21][CH2:20]2)=[O:18])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:27][C:28]1[CH:29]=[N:30][C:31](Cl)=[N:32][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Br:27][C:28]1[CH:29]=[N:30][C:31]([NH:26][CH2:25][CH:22]2[CH2:21][CH2:20][N:19]([C:17]([C@@H:15]3[CH2:16][C@H:14]3[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)=[O:18])[CH2:24][CH2:23]2)=[N:32][CH:33]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 69222876HCID 69222876, compound

Product 1

HCID 58635320HCID 58635320, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (1-{[(1R,2R)-2-phenylcyclopropyl]carbonyl}piperidin-4-yl)methylamine trifluoroacetate salt (1.00 g, 2.69 mmol), 5-bromo-2-chloro-pyrimidine ([32779-36-5 ], 0.519 g, 2.69 mmol) and cesium carbonate (1.75 g, 5.37 mmol) in DMF (7 mL) was heated at 100° C. for 1.5 h. The reaction mixture was cooled to RT, diluted with ethyl acetate (200 mL), washed with water (5×20 mL), and brine (10 mL), then dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel 60, eluting with 10:1–20:89–70 CH2Cl2:2-propanol:hexane to give the title compound. (0.31 g, 28.1%). M.S. (M+1): 416.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed with water (5×20 mL), and brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel 60
  7. washeluting with 10:1–20:89–70 CH2Cl2

Sources & evidence

ORD record
ord-5facbf71991f45fdb07fb96c0ea2b127
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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