HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → [4-(N,N-dimethylamino)quinazolin-6-yl]acrylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Acrylic Acid | HCID 6581 | — |
| Reactant | Dimethylacetamide | HCID 31374 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | Dichloromethane ethylacetate | HCID 21226138 | — |
| Solvent | Methylenechloride Hexane | HCID 21226440 | — |
| Solvent | Dichloromethane ethyl acetate methanol | HCID 21901258 | — |
| Product | [4-(N,N-dimethylamino)quinazolin-6-yl]acrylamide | HCID 18176137 | 42% |
Reaction Steps
To a stirred solution containing the above 4-N,N-dimethylamino-6-aminoquinazoline (0.65 g, 3.45 mmol), acrylic acid (4 mol eq., 13.8 mmol, 0.95 mL), and pyridine (excess, 1.3 mL) in DMA (20 mL) under N2 was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI.HCl) (2 mol eq., 6.90 mmol, 1.32 g). The standard procedure above was followed to give after chromatography on silica gel eluting with EtOAc/CH2Cl2 (1:1) to MeOH/CH2Cl2/EtOAc (1:4:5), [4-(N,N-dimethylamino)quinazolin-6-yl]acrylamide (350 mg, 42%) as a cream powder, mp (CH2Cl2/hexane) 204-206° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06602863B1 |
| Source dataset | uspto-grants-2003_08 |
| ORD ID | ord-fbf95f60aa1445efa08e9b6b71dab0f9 |
| Source note | uspto-grants-2003_08 |