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

HRID 536726Notes

Reaction equation

HRID 536726 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-7336eb4a46ff4828a95254fbb36aceb0
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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