HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetonitrile → [2-Methylsulfanyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-yl]-(4-trifluoromethyl-phenyl)-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | 4-Chloro-2-methylsulfanyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine | HCID 86615308 | — |
| Reactant | HCID 178503519 | HCID 178503519 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | [2-Methylsulfanyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-yl]-(4-trifluoromethyl-phenyl)-amine | HCID 58972614 | 89% |
Reaction Steps
4-Chloro-2-methylsulfanyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine. To a solution of 2-methylsulfanyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-ol (1.8 g, 4.92 mmol) in CH3CN (40 mL) was added POCl3 (1.4 mL, 14.8 mmol). After 15 min at 80° C., the mixture was cooled to rt, diluted with EtOAc, and quenched slowly with satd. aq. NaHCO3. The organic layer was separated, dried (MgSO4), and concentrated. The crude residue was purified (FCC) to give the title compound (1.6 g, 89%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09422293B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-24aa807b883f4f6eb29f6011eb3a880f |
| Source note | uspto-grants-2016_08 |