Tyramine → HCID 59643255, compound

HRID 2251480Notes

Reaction equation

HRID 2251480 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(N(C(C)C)CC)(C)C.Cl[C:21]1[N:26]=[CH:25][C:24]([CH2:27][CH3:28])=[CH:23][N:22]=1>CN(C=O)C>[CH2:27]([C:24]1[CH:23]=[N:22][C:21]([NH:1][CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=2)=[N:26][CH:25]=1)[CH3:28]

Participants

5

Reactant 3

HCID 5610TyramineHCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidine

Product 1

HCID 59643255HCID 59643255, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tyramine (5.52 g, 0.040 mol) in 40 ml of anhydrous DMF was treated with diisopropylethylamine (6.1 ml, 0.035 mol). After stirring at rt for 15 minutes, 2-chloro-5-ethylpyrimidine (4.25 ml, 0.035 mol) was added and the mixture heated at 80° C. for 14 hours. The solution was allowed to cool to room temperature and was partitioned between equal volumes of water and ethyl acetate. The aqueous phase was washed with ethyl acetate and the combined organic phases were dried over MgSO4 and concentrated. The residue was purified by flash chromatography eluting with 40% ethyl acetate-hexane to afford the title compound as a colorless solid (4.94 g; 58% yield).

Workup

  1. temperaturethe mixture heated at 80° C. for 14 hours
  2. temperatureto cool to room temperature
  3. customwas partitioned between equal volumes of water and ethyl acetate
  4. washThe aqueous phase was washed with ethyl acetate
  5. dry with materialthe combined organic phases were dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 40% ethyl acetate-hexane

Sources & evidence

ORD record
ord-fb3bd5d82e324c479975ab0269ea1699
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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