(e)-3-(4-Chlorophenyl)-n-[1-(2,2-diethoxyethyl)-2-oxo-1,2-dihydropyrimidin-4-yl]-acrylamide → (e)-3-(4-Chloro-phenyl)-n-[1-(2,2-dihydroxy-ethyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acrylamide

HRID 1425648Notes

Reaction equation

HRID 1425648 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C:13]2[CH:18]=[CH:17][N:16]([CH2:19][CH:20]([O:24]CC)[O:21]CC)[C:15](=[O:27])[N:14]=2)=[O:11])=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C:13]2[CH:18]=[CH:17][N:16]([CH2:19][CH:20]([OH:24])[OH:21])[C:15](=[O:27])[N:14]=2)=[O:11])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68902508(e)-3-(4-Chlorophenyl)-n-[1-(2,2-diethoxyethyl)-2-oxo-1,2-dihydropyrimidin-4-yl]-acrylamide

Product 1

HCID 57959562(e)-3-(4-Chloro-phenyl)-n-[1-(2,2-dihydroxy-ethyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acrylamideYield 100%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(E)-3-(4-chloro-phenyl)-N-[1-(2,2-diethoxy-ethyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acrylamide (c, 2.48 g, 6.8 mM) was dissolved in trifluoroacetic acid (37 mL) and stirred at room temperature for 4.5 hours. Trifluoroacetic acid was removed in vacuo, and toluene (40 mL) was added to remove the solvent in vacuo. The residual solid was added with ethyl acetate (15 mL) and 5% aqueous sodium bicarbonate (15 mL) and stirred at room temperature. The precipitated crystal was filtered to afford 2.28 g of the desired compound (E)-3-(4-chloro-phenyl)-N-[1-(2,2-dihydroxy-ethyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acrylamide (d) (yield 100%, colorless crystal).

Workup

  1. customTrifluoroacetic acid was removed in vacuo, and toluene (40 mL)
  2. additionwas added
  3. customto remove the solvent in vacuo
  4. additionThe residual solid was added with ethyl acetate (15 mL) and 5% aqueous sodium bicarbonate (15 mL)
  5. stirringstirred at room temperature
  6. filtrationThe precipitated crystal was filtered

Sources & evidence

ORD record
ord-3afd7c77fb014b4d8dd458b74a24ac23
Source dataset
uspto-grants-2015_01
Patent number
US08933012B2

Reaction notes

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