Triethylamine → HCID 21081020, compound

HRID 548956Notes

Reaction equation

HRID 548956 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:7])[CH3:6].C(N(CC)CC)C.[Br:15][C:16]1[C:17](Cl)=[N:18][C:19]([Cl:22])=[N:20][CH:21]=1>C(#N)C.C(OCC)(=O)C>[Br:15][C:16]1[C:17]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:7])[CH3:6])=[N:18][C:19]([Cl:22])=[N:20][CH:21]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66082N-(2-aminoethyl)acetamideHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 21081020HCID 21081020, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.14 ml (1.42 mmol) of N-(2-aminoethyl)acetamide and 0.22 ml (1.60 mmol) of triethylamine are added to a solution of 300 mg (1.32 mmol) of 5-bromo-2,4-dichloro-pyrimidine in 4.2 ml of acetonitrile at room temperature. The mixture is stirred at room temperature for 24 hours and then diluted with ethyl acetate. It is washed with saturated NaCl solution, 10% strength citric acid solution and saturated NaHCO3 solution. The organic phase is dried (Na2SO4), filtered and concentrated. The resulting residue is recrystallized from ethyl acetate. 294 mg (1.00 mmol; yield: 75%) of the product are obtained.

Workup

  1. washIt is washed with saturated NaCl solution, 10% strength citric acid solution and saturated NaHCO3 solution
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue is recrystallized from ethyl acetate
  6. custom294 mg (1.00 mmol; yield: 75%) of the product are obtained

Sources & evidence

ORD record
ord-c073261760f641afa08e068ed88506fa
Source dataset
uspto-grants-2011_05
Patent number
US07943629B2

Reaction notes

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