TBAF tetrahydrofuran → HCID 69434160, compound

HRID 1890662Notes

Reaction equation

HRID 1890662 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([C:14]1[N:19]=[CH:18][C:17]([CH2:20][O:21][Si](C(C)(C)C)(C)C)=[CH:16][N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:29])[N:7]([C:14]1[N:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 69434076HCID 69434076, compound

Product 1

HCID 69434160HCID 69434160, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

[5-(tert-Butyldimethylsiloxymethyl)pyrimidin-2-yl]phenylcarbamic acid tert-butyl ester (560 mg, 1.34 mmol) obtained in Step 5 was dissolved in THF (10 mL), and a 1.0 mol/L tetrabutylammonium fluoride-THF solution (4.02 mL, 4.02 mmol) was added to the solution, followed by stirring at room temperature for 1.5 hours. The reaction mixture was diluted with ethyl acetate and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:1) to obtain (5-hydroxymethylpyrimidin-2-yl)phenylcarbamic acid tert-butyl ester (336 mg, 83%).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:1)

Sources & evidence

ORD record
ord-9605ff63f4b747e79d552e0a6a107c20
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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