Cesium carbonate → HCID 88006737, compound

HRID 1582521Notes

Reaction equation

HRID 1582521 reaction equation
[CH3:1][Si:2]([CH3:28])([CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[N:14][CH:15]=1.[CH3:29][Si:30]([CH3:67])([CH2:46][CH2:47][C:48]([F:66])([F:65])[C:49]([F:64])([F:63])[C:50]([F:62])([F:61])[C:51]([F:60])([F:59])[C:52]([F:58])([F:57])[C:53]([F:56])([F:55])[F:54])[CH2:31][CH2:32][CH2:33][CH2:34]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:67][Si:30]([CH3:29])([CH2:46][CH2:47][C:48]([F:65])([F:66])[C:49]([F:63])([F:64])[C:50]([F:62])([F:61])[C:51]([F:59])([F:60])[C:52]([F:57])([F:58])[C:53]([F:54])([F:55])[F:56])[CH2:31][CH2:32][CH2:33][CH2:34][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[N:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:28])[CH2:23][Si:24]([CH3:25])([CH3:26])[CH3:27])=[CH:15][N:14]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 88006719HCID 88006719, compoundHCID 136028022HCID 136028022, compound

Product 1

HCID 88006737HCID 88006737, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-{5-[6-(dimethyltrimethylsilanylmethyl-silanyl)-hexyloxy]-pyrimidin-2-yl}-phenol (0.083 g, 0.200 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 (0.126 g, 0.200 mmol) and cesium carbonate (0.078 g, 0.24 mmol) in DMF (10 ml) was stirred at room temperature for 24 h. The reaction mixture was washed with water and the organic layer extracted into ethyl acetatelhexane (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 acetatelhexane (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-21039085a5db4c2f9d7793e7b72b034d
Source dataset
uspto-grants-2004_05
Patent number
US06737124B2

Reaction notes

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