Tetrabutylammonium Fluoride → 3-Chlorophenylurea

HRID 1696563Notes

Reaction equation

HRID 1696563 reaction equation
C(C1C=C([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)=[O:12])N(C2C=CC=C(CO[Si](C(C)(C)C)(C)C)C=2)N=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:20][C:16]1[CH:15]=[C:14]([NH:13][C:11](=[O:12])[NH2:10])[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67271647HCID 67271647, compound

Product 1

HCID 160753-ChlorophenylureaYield 166.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-t-butyl-1-{3-[(t-butyldimethylsilyloxy)methyl]phenyl}-1H-pyrazol-5-yl)-3-(3-chlorophenyl)urea (120 mg, 0.12 mmol) in THF (2 mL) was added TBAF (1.0 M, 0.13 mL, 0.13 mmol). The reaction mixture was stirred at RT for 2.5 h. The solvent was removed under reduced pressure. EtOAc was added into the residue followed by 1N—HCl (5 drops). The combined organic extracts were washed with brine, dried (Na2SO4), filtered, concentrated and purified via column chromatography to yield 1-(3-t-butyl-1-(3-hydroxymethyl)phenyl)-1H-pyrazol-5-yl)-3-(3-chlorophenyl)urea as a white powder (34 mg, 71% yield). 1H-NMR (CDCl3): δ 8.11 (s, 1H), 7.34 (t, J=2.0 Hz, 1H), 7.05-7.25 (m, 7H), 6.99 (dt, J=1.3, and 7.8 Hz, 1H), 6.39 (s, 1H), 4.39 (s, 2H), 1.33 (s, 9H); MS (EI) m/z: 399 (M+H+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionEtOAc was added into the residue
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified via column chromatography

Sources & evidence

ORD record
ord-dfe9c53f38b44b28a1aa2e8c950d6d0d
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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