Hydrofluoric Acid → HCID 18753263, compound

HRID 1838142Notes

Reaction equation

HRID 1838142 reaction equation
F.C([Si](C)(C)[O:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([N:22]2[CH2:27][CH2:26][CH:25]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[CH2:24][CH2:23]2)[N:16]=[C:15]([CH3:35])[N:14]=1)(C)(C)C>C(#N)C.ClCCl>[F:34][C:31]1[CH:32]=[CH:33][C:28]([CH:25]2[CH2:26][CH2:27][N:22]([C:17]3[N:16]=[C:15]([CH3:35])[N:14]=[C:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][OH:7])[C:18]=3[N+:19]([O-:21])=[O:20])[CH2:23][CH2:24]2)=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 14917Hydrofluoric AcidHCID 18753284HCID 18753284, compound

Product 1

HCID 18753263HCID 18753263, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

0.590 g (14.5 mmol) of hydrofluoric acid (47-51% in water) were slowly added to a solution of 0.375 g (0.723 mmol) of the 4-[4-(tert-butyl-dimethyl-silanyloxy)-butoxy]-6-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methyl-5-nitro-pyrimidine in 10.0 ml of acetonitrile and 5.0 ml of dichloromethane. The reaction mixture was then stirred at room temperature for 1 hour. It was then poured into 50 ml of an ice/water mixture and extracted 3 times with 50 ml of dichloromethane. The combined dichloromethane phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 9:1 to 1:1 v/v gradient of hexane and ethylacetate as the eluent giving 0.181 g (0.448 mmol, 61.9% of theory) of the 4-{6-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methyl-5-nitro-pyrimidin-4-yloxy}-butan-1-ol as a light yellowish oil; MS: [M+H]+=405.

Workup

  1. extractionextracted 3 times with 50 ml of dichloromethane
  2. dry with materialThe combined dichloromethane phases were dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue formed
  5. customwas chromatographed on silica gel with a 9:1 to 1:1 v/v gradient of hexane and ethylacetate as the eluent

Sources & evidence

ORD record
ord-9bead5d3e777442fa264f715a5d15343
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

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