Cesium carbonate → HCID 22677056, compound

HRID 1837426Notes

Reaction equation

HRID 1837426 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][N:11]=1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]=[CH2:32].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=[CH2:25])[CH:5]=[CH:4][C:3]=1[C:10]1[N:11]=[CH:12][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 759078-Bromooct-1-eneHCID 135585898HCID 135585898, compound

Product 1

HCID 22677056HCID 22677056, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 2-(2,3-difluoro-4-hydroxyphenyl)-5-octylpyrimidine (1.00 g, 3.07 mmol), 8-bromo-1-octene (0.59 g, 3.07 mmol) and cesium carbonate (1.99 g, 6.14 mmol) in acetone (70 ml) was heated under reflux for 18 h. The reaction mixture was cooled to room temperature, washed with water and the organic layer extracted in ethyl acetate/hexane (3 times, 1:1). The combined extracts were washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residues were purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1), Rf 0.30] and recrystallized from hexane to yield colorless crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. washwashed with water
  4. extractionthe organic layer extracted in ethyl acetate/hexane (3 times, 1:1)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customThe residues were purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1), Rf 0.30]
  9. customrecrystallized from hexane
  10. customto yield colorless crystals

Sources & evidence

ORD record
ord-979da43545a749598cc515c3150a55c0
Source dataset
uspto-grants-2004_08
Patent number
US06783812B2

Reaction notes

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