Ethyl Acetate → 2-(3-Phenyl-pyridin-2-yl)-acetamidine

HRID 2169233Notes

Reaction equation

HRID 2169233 reaction equation
C(O[NH:5][C:6](=[NH:20])[CH2:7][C:8]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)(=O)C.C(OCC)(=O)C>C(O)C.[Pd]>[C:14]1([C:13]2[C:8]([CH2:7][C:6]([NH2:20])=[NH:5])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 178476706HCID 178476706, compound

Product 1

HCID 867258802-(3-Phenyl-pyridin-2-yl)-acetamidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred degassed solution of (161) (2.7 g, 10.04 mmol) in ethanol (135 mL) was added 10% Pd—C (270 mg), the mixture was stirred 16 h under H2 (hydrogen bubbler) at room temperature. Silica thin layer chromatography was performed (ethyl acetate, Rf=0.1). The reaction mixture was filtered through celite, washed with 10% methanol in dichloromethane (5×100 mL), dried and concentrated. The yellow solid was washed with 10% ethyl acetate in hexane (3×30 mL) to get pure 2-(3-phenyl-pyridin-2-yl)-acetamidine with acetic acid (162) (1.7 g, 62.5%) as an off-white solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with 10% methanol in dichloromethane (5×100 mL)
  3. customdried
  4. concentrationconcentrated
  5. washThe yellow solid was washed with 10% ethyl acetate in hexane (3×30 mL)

Sources & evidence

ORD record
ord-2d88b46f1a444f838aaf9c6917fad805
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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