Acetic Acid → 3,3-diphenyl-N-(2-(pyrimidin-2-yl)ethyl)propan-1-amine

HRID 2190307Notes

Reaction equation

HRID 2190307 reaction equation
[CH:1]([C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1)=[CH2:2].CC(O)=O.[C:13]1([CH:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:20][CH2:21][NH2:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCO>[C:23]1([CH:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:20][CH2:21][NH:22][CH2:2][CH2:1][C:3]2[N:8]=[CH:7][CH:6]=[CH:5][N:4]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 796983,3-DiphenylpropylamineHCID 101250522-Ethenylpyrimidine

Product 1

HCID 575863733,3-diphenyl-N-(2-(pyrimidin-2-yl)ethyl)propan-1-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-vinylpyrimidine (0.373 g, 3.51 mmol) in EtOH (6 mL) at room temperature was added AcOH (1 mL) and 3,3-diphenylpropan-1-amine (2.21 g, 10.5 mmol). The reaction mixture was heated to reflux for 1 d, cooled to 0° C., and the solids were removed by filtration. The filtrate was concentrated and diluted with 5 M NaOH, brine, and EtOAc. The aqueous phase was extracted with EtOAc (2×) and the combined organic extracts were washed with brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 10% MeOH in DCM) gave 3,3-diphenyl-N-(2-(pyrimidin-2-yl)ethyl)propan-1-amine.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 d
  3. customthe solids were removed by filtration
  4. concentrationThe filtrate was concentrated
  5. additiondiluted with 5 M NaOH, brine, and EtOAc
  6. extractionThe aqueous phase was extracted with EtOAc (2×)
  7. washthe combined organic extracts were washed with brine (1×)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by flash column chromatography on silica gel (eluted with 10% MeOH in DCM)

Sources & evidence

ORD record
ord-d5ec48588dde48cb9e59f8792d53ebfd
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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