HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hexane → HCID 66976956, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-Bromo-2-chloropyrimidine | HCID 606665 | — |
| Reactant | HCID 66977146 | HCID 66977146 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 66976956 | HCID 66976956 | 45% |
Reaction Steps
To a solution of ethyl 4-(methylsulfonyl)piperidine-4-carboxylate hydrochloride (0.20 g, 0.74 mmol) in EtOH (7.0 mL) was added DIPEA (0.03 mL, 1.86 mmol) at rt and the mixture stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (0.12 g, 0.62 mmol). The reaction was then heated up to 70° C. for 1 h. After completion (by TLC), solvent was evaporated and the crude residue purified over 100-200 M silica-gel using 15% EtOAc:hexane to obtain the desired product as a yellow solid (0.108 g, 45% yield). 1H NMR (DMSO-d6): δ 1.20 (t, J=7.20 Hz, 3H), 1.62 (m, 2H), 2.07 (m, 2H), 2.69 (m, 2H), 3.69 (s, 3H), 4.62 (q, J=7.20 Hz, 2H), 4.86 (m, 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-30db6f5a73b9456bad1d196e2e96498a |
| Source note | uspto-grants-2015_11 |