HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 2-[6-(4-Chloro-benzyl)-2-(piperidin-4-ylamino)-pyrimidin-4-yl]-propan-2-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-[4-(4-Chloro-benzyl)-6-(1-hydroxy-1-methyl-ethyl)-pyrimidin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester | HCID 67342026 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-[6-(4-Chloro-benzyl)-2-(piperidin-4-ylamino)-pyrimidin-4-yl]-propan-2-ol | HCID 67341833 | 119% |
Reaction Steps
To a solution of 4-[4-(4-chloro-benzyl)-6-(1-hydroxy-1-methyl-ethyl)-pyrimidin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester (220 mg, 0.447 mmol) in dichloromethane (5 mL) was added at 0° C. trifluoroacetic acid (365 μL, 4.77 mmol) and the mixture was stirred for 18 hours while allowing to warm to ambient temperature. It was basified by addition of 1 M aqueous sodium carbonate solution (5 mL) and extracted with dichloromethane (15 mL). The organic layers were washed with 1 M aqueous sodium carbonate solution (15 mL) and dried over sodium sulfate. Concentration afforded the title compound (192 mg, 99%) as a brown semi-solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08486967B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-763f30b5d33b4910824d52da657a436f |
| Source note | uspto-grants-2013_07 |