Cesium carbonate → HCID 22717476, compound

HRID 1582522Notes

Reaction equation

HRID 1582522 reaction equation
[CH2:1]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[N:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:24][Si:25]([CH3:62])([CH2:41][CH2:42][C:43]([F:61])([F:60])[C:44]([F:59])([F:58])[C:45]([F:57])([F:56])[C:46]([F:55])([F:54])[C:47]([F:53])([F:52])[C:48]([F:51])([F:50])[F:49])[CH2:26][CH2:27][CH2:28][CH2:29]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:29][CH2:28][CH2:27][CH2:26][Si:25]([CH3:62])([CH3:24])[CH2:41][CH2:42][C:43]([F:61])([F:60])[C:44]([F:58])([F:59])[C:45]([F:56])([F:57])[C:46]([F:54])([F:55])[C:47]([F:52])([F:53])[C:48]([F:49])([F:50])[F:51])=[CH:21][CH:22]=2)=[N:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 88006719HCID 88006719, compoundHCID 135585902Phenol, 4-(5-decyl-2-pyrimidinyl)-

Product 1

HCID 22717476HCID 22717476, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-(5-decyl-pyrimidin-2-yl)-phenol (3.744 g, 13.00 mmol), toluene-4-sulfonic acid 4-[dimethyl-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-silanyl]-butyl ester (7.58 g, 13.00 mmol) and cesium carbonate (4.69 g, 14.4 mmol) in DMF (35 ml) was stirred at room temperature for 24 h. The reaction mixture was washed with water and the organic layer extracted into ethyl acetate/hexane (3×20 ml, 1:1). The combine extracts were washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residues were purified by column chromatography [silica gel, hexane/ethyl acetate (9:1)] to yield a colorless solid, which was recrystallized from acetonitrile.

Workup

  1. washThe reaction mixture was washed with water
  2. extractionthe organic layer extracted into ethyl acetate/hexane (3×20 ml, 1:1)
  3. washThe combine extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe residues were purified by column chromatography [silica gel, hexane/ethyl acetate (9:1)]
  7. customto yield a colorless solid, which
  8. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-8db9bc94822f42a1b32954a12e855790
Source dataset
uspto-grants-2004_05
Patent number
US06737124B2

Reaction notes

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