HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hexane → HCID 66977197, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-Bromo-2-chloropyrimidine | HCID 606665 | — |
| Reactant | HCID 66977253 | HCID 66977253 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 66977197 | HCID 66977197 | 60% |
Reaction Steps
To a solution of ethyl 4-(methylthio)piperidine-4-carboxylate hydrochloride (0.17 g, 0.75 mmol) in EtOH (10.0 mL) was added DIPEA (0.60 mL, 3.75 mmol) at rt and the mixture stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (0.18 g, 0.90 mmol). The reaction was heated up to 70° C. for 1 h. After completion of reaction (by TLC), solvent was evaporated and the crude residue purified over 100-200 M silica-gel using 3.0% EtOAc:hexane to obtain the desired product as a white solid (0.16 g, 60% yield). 1H NMR (DMSO-d6): δ 1.18 (t, J=7.20 Hz, 3H), 1.70 (m, 2H), 2.04 (s, 3H), 2.14 (m, 2H), 3.50 (m, 2H), 4.00 (m, 2H), 4.20 (q, J=7.20 Hz, 2H), and 8.46 (s, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181234B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-3e0a548ac1b349969646a27fb3f58fc9 |
| Source note | uspto-grants-2015_11 |