Hydrochloric Acid → (5)-5-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)pyrimidin-2(1H)-one

HRID 1618053Notes

Reaction equation

HRID 1618053 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:13]=[N:14][C:15]([O:18]C)=[N:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+].C(OCC)(=O)C>O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:13]=[N:14][C:15](=[O:18])[NH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 67015720(S)-3-(4-Bromophenyl)-1-(2-methoxypyrimidin-5-yl)-3-o-tolylpropan-1-one

Product 1

HCID 66668697(5)-5-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)pyrimidin-2(1H)-oneYield 97.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-3-(4-bromophenyl)-1-(2-methoxypyrimidin-5-yl)-3-o-tolylpropan-1-one (700 mg, 1.53 mmol, Eq: 1.00) in dioxane (18 mL) was added 37% aq. hydrochloric acid solution (2.56 mL, 30.6 mmol) and the resulting solution was first stirred at ambient temperature for 45 min and then 2½ h at 60° C., then poured onto sat. aq. sodium hydrogencarbonate solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; gradient dichloromethane to dichloro-methane/methanol/25% aq. ammonia solution 90:10:0.25) produced the title compound (592 mg, 97%). White solid, MS (ESI+): m/z=: 397.0 [M+H]+.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-7d665c4d6be94dc484a826077daccae7
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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