HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Hydroxide → 3-(4-Amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Dimethylbarbituric acid | HCID 69860 | — |
| Reactant | 3-(2-Chloro-4-diallylamino-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol | HCID 57421289 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-(4-Amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol | HCID 86629109 | 76.5% |
Reaction Steps
A solution of 1,3-dimethylbarbituric acid ([CAS Reg. No. 769-42-6], 828 mg), tetrakis(triphenylphosphine) palladium (0) (230 mg) and 3-(2-Chloro-4-diallylamino-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (590 mg) in DCM (120 ml) was heated under reflux for 3 h. NaOH (1N aq) was added and extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, ethyl acetate/heptane 0:100-50:50) to give the title compound as a light yellow gum (370 mg). MS (m/e)=365.0 [M+H+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08883786B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-d58ce1897b754bd99e6b451a7d5a2c50 |
| Source note | uspto-grants-2014_11 |