HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (S)-Ethyl 2-chloro-4-(1-(5-fluoropyridin-2-yl)ethylamino)pyrimidine-5-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Ethyl 2,4-dichloropyrimidine-5-carboxylate | HCID 104020 | — |
| Reactant | (S)-1-(5-fluoropyridin-2-yl)ethanamine hydrochloride | HCID 67123789 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (S)-Ethyl 2-chloro-4-(1-(5-fluoropyridin-2-yl)ethylamino)pyrimidine-5-carboxylate | HCID 123343309 | 115.2% |
Reaction Steps
A solution of ethyl 2,4-dichloropyrimidine-5-carboxylate (prepared as described in WO2009/131687, 0.29 g, 1.31 mmol), (S)-1-(5-fluoropyridin-2-yl)ethanamine hydrochloride (prepared as described in WO2006/123113, 0.28 g, 1.59 mmol) and diisopropylethylamine (0.69 mL, 3.96 mmol) in acetonitrile (3 mL) was stirred overnight at ambient temperature. Water was then added and the reaction mixture was extracted with diethyl ether. The organic phase was washed with water and brine, dried (MgSO4), filtered and the solvents evaporated under reduced pressure to yield the title compound (0.49 g, 85%) as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09034311B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-f003129489d548f5a4f2c7df81b6bbb5 |
| Source note | uspto-grants-2015_05 |