Acetic Acid → N-benzyl-2-(pyrimidin-2-yl)ethanamine

HRID 2190320Notes

Reaction equation

HRID 2190320 reaction equation
[CH:1]([C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1)=[CH2:2].CC(O)=O.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCO>[CH2:13]([NH:20][CH2:2][CH2:1][C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7504BenzylamineHCID 101250522-Ethenylpyrimidine

Product 1

HCID 68724585N-benzyl-2-(pyrimidin-2-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-vinylpyrimidine (1.55 g, 14.6 mmol) in EtOH (15 mL) at room temperature was added AcOH (2.0 mL) and benzylamine (3.14 g, 29.3 mmol) (3.2 mL). The reaction mixture was heated to reflux for 18 h, and concentrated. Diluted with EtOAc, washed with 5 M NaOH (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 2% to 10% MeOH in DCM) gave N-benzyl-2-(pyrimidin-2-yl)ethanamine.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. concentrationconcentrated
  4. additionDiluted with EtOAc
  5. washwashed with 5 M NaOH (1×), brine (1×)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash column chromatography on silica gel (eluted with 2% to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-0d326be835d64035bb0f0b90796b21bf
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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