Hydrochloric Acid → 6-[(1,1-Dimethylethyl)thio]-3-pyridinemethanamine

HRID 911645Notes

Reaction equation

HRID 911645 reaction equation
[C:1]([S:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].Cl>C1COCC1.CO>[NH2:11][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 28413190864266-67-1

Product 1

HCID 435287746-[(1,1-Dimethylethyl)thio]-3-pyridinemethanamineYield 61.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Use a method similar to the General Procedure 6-5 to react 6-(tert-butylthio)nicotinonitrile (4.4 g, 22.7 mmol) in anhydrous THF (25 mL) with 1M BH3-THF complex in THF (25 mL, 25 mmol). Add 5M aqueous HCl (10 mL) cautiously and stir the mixture overnight at room temperature. Extract into EtOAc, wash with brine, dry over MgSO4 and concentrate in vacuo to give an orange solid. Dissolve the crude mixture in methanol and filter through an SCX column eluting with methanol followed by 3M ammonia in methanol to obtain the title compound (2.74 g, 61%). MS (ES+) m/z: 197 (M+H)+.

Workup

  1. extractionExtract into EtOAc
  2. washwash with brine
  3. dry with materialdry over MgSO4
  4. concentrationconcentrate in vacuo
  5. customto give an orange solid
  6. filtrationfilter through an SCX column
  7. washeluting with methanol

Sources & evidence

ORD record
ord-69df268f146a47289309304c78373329
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…