HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → N-{4-[(3-bromophenyl)amino]pyrido[3,4-d]pyrimidin-6-yl}-2-methylprop-2-enamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methacryloyl chloride | HCID 13528 | — |
| Reactant | 4-N-(3-bromophenyl)pyrido[3,4-d]pyrimidine-4,6-diamine | HCID 5328258 | — |
| Reactant | Dichloromethane ethylacetate | HCID 21226138 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Methylenechloride Hexane | HCID 21226440 | — |
| Product | N-{4-[(3-bromophenyl)amino]pyrido[3,4-d]pyrimidin-6-yl}-2-methylprop-2-enamide | HCID 5329071 | 6% |
Reaction Steps
To a solution of 6-amino-4-[(3-bromophenyl)-amino]pyrido[3,4-d]pyrimidine (J Med Chem, 1996;39:1823) (250 mg, 0.82 mmol), Et3N (excess, 2.0 mL) and DMAP (catalytic) in THF (30 mL) under nitrogen was added methacryloyl chloride (3×1.1 mol eq., total of 264 μL), the reaction conditions and work up were followed as above to give after column and preparative layer chromatography on silica gel eluting with EtOAc/CH2Cl2 (1:1), N-[4-[(3-bromophenyl)amino]-pyrido-[3,4-d]pyrimidin-6-yl]-2-methylacrylamide (18 mg, 6%) as a cream powder, mp (CH2Cl2/hexane) 177-178° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06602863B1 |
| Source dataset | uspto-grants-2003_08 |
| ORD ID | ord-68726ddc595148daafe3ae62f6fa68f3 |
| Source note | uspto-grants-2003_08 |