HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (5)-5-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)pyrimidin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (S)-3-(4-Bromophenyl)-1-(2-methoxypyrimidin-5-yl)-3-o-tolylpropan-1-one | HCID 67015720 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (5)-5-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)pyrimidin-2(1H)-one | HCID 66668697 | 97.4% |
Reaction Steps
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]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08765730B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-7d665c4d6be94dc484a826077daccae7 |
| Source note | uspto-grants-2014_07 |