Trifluoroacetic acid → 5-Amino-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile

HRID 1504756Notes

Reaction equation

HRID 1504756 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[CH:8]=[C:9]([NH:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[N:17]=2)[C:10]([C:13]#[N:14])=[N:11][CH:12]=1.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[NH2:6][C:7]1[CH:8]=[C:9]([NH:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[N:17]=2)[C:10]([C:13]#[N:14])=[N:11][CH:12]=1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867316525-[(2,4-Dimethoxybenzyl)amino]-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile

Product 1

HCID 867316535-Amino-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of 5-[(2,4-dimethoxybenzyl)amino]-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile (240 mg, 0.62 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (0.96 mL, 12.5 mmol) dropwise, and the reaction mixture was stirred for 10 minutes. The reaction mixture was diluted with ethyl acetate and aqueous saturated sodium bicarbonate. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-65% ethyl acetate/hexanes, linear gradient) to afford 5-amino-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile. MS ESI calc'd for C13H14N5 [M+H]+ 240. found 240. 1H NMR (500 MHz, DMSO-d6) δ 8.59 (s, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.36 (d, J=2.2 Hz, 1H), 6.57 (s, 1H), 6.55 (s, 1H), 6.25 (s, 2H), 2.28 (s, 3H), 2.18 (s, 3H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (0-65% ethyl acetate/hexanes, linear gradient)

Sources & evidence

ORD record
ord-ebb5d461b7ba47b38ba3bf000e50a1f8
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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