HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → HCID 90405754, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Chloro-5-(trifluoromethyl)pyrimidine | HCID 13317019 | — |
| Reactant | HCID 68440174 | HCID 68440174 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 90405754 | HCID 90405754 | 72.3% |
Reaction Steps
To (2S,3R)-tert-butyl 3-hydroxy-2-methylpiperidine-1-carboxylate (670 mg, prepared according to J. Org. Chem. 2008, 73, 2898) in THF (15 mL) at 0° C. was added NaH (60 wt %, 188 mg). After 15 min, 2-chloro-5-(trifluoromethyl)pyrimidine (570 mg) was added and the reaction allowed to proceed at rt overnight. The reaction was diluted with H2O and extracted with DCM. The organic layers were dried (MgSO4). Purification via silica gel chromatography (0-40% EtOAc in heptane) gave the title compound (813 mg, 72%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09115117B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-565ff7de5f784e06b0206158f80a0d94 |
| Source note | uspto-grants-2015_08 |