HuagongsheHuagongshe Chemistry Print Report · For research reference only
Amantadine → N2-[4-(dimethylphosphoryl)phenyl]-N'-(tricyclo[3.3.1.13,7]dec-1-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Amantadine | HCID 2130 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-chloro-N-[4-(dimethylphosphoryl)phenyl]-5-(trifluoromethyl)pyrimidin-2-amine | HCID 86668788 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | N2-[4-(dimethylphosphoryl)phenyl]-N'-(tricyclo[3.3.1.13,7]dec-1-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine | HCID 68165076 | 8% |
Reaction Steps
To a solution of 4-chloro-N-[4-(dimethylphosphoryl)phenyl]-5-(trifluoromethyl)pyrimidin-2-amine (prepared as in Example 1: 27 mg, 0.078 mmol) in 1.5 mL of ethanol was added 10 μL of triethylamine and 1-Adamantanamine (12 mg, 0.078 mmol). The mixture was microwave at 120 degrees for 20 minutes. The reaction mixture was filtered through a syringe filter and purified by prep-HPLC (Waters Sunfire C18 column with ACN/water mobile phases) to yield a white solid as product (3 mg, 8% yield.) MS/ES+: m/z=465.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09012462B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-c94759b9132b4571b4872596f0bffb66 |
| Source note | uspto-grants-2015_04 |