Trifluoroacetic acid → 5-Tert-butylpyridin-2-amine

HRID 1931090Notes

Reaction equation

HRID 1931090 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:11]C(=O)OC(C)(C)C)=[N:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH2:11])=[N:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66642981Tert-butyl 5-tert-butylpyridin-2-ylcarbamate

Product 1

HCID 205879625-Tert-butylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of Example 59A (1.0 g, 40 mmol) in dichloromethane (3 mL) was added trifluoroacetic acid (3. mL, 40 mmol). The reaction mixture was stirred at ambient temperature for 3 hours then concentrated under reduced pressure. The residue was diluted with ethyl acetate (100 mL) and washed with saturated aqueous NaHCO3. The layers were separated and the aqueous phase was extracted with ethyl acetate (5×100 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide the title compound. MS (ESI+) m/z 151 (M+H)+.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate (100 mL)
  3. washwashed with saturated aqueous NaHCO3
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate (5×100 mL)
  6. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb5d937d6d6642d18149dea1d4003d09
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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