2,4,6-Trimethylpyridine → HCID 18326535, compound

Participants

Reaction Steps

To 450 mg (2.17 mmol) of 6-nitroquinazoline-2,4(1H,3H)-dione were added 4.50 ml (48.28 mmol) of phosphorus oxychloride and 658 mg (5.43 mmol) of collidine, and the resulting mixture was subjected to heating under reflux for 24 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 10 ml of acetonitrile, followed by adding thereto 320 mg (2.29 mmol) of 2-propoxyethylamine hydrochloride and 3.51 ml (25.18 mmol) of triethylamine under ice cooling and stirring under ice cooling for 30 minutes. After water was added to the reaction solution, crystals thus precipitated were filtered to give 2-chloro-6-nitro-4-(2-propoxyethylamino)quinazoline. 5.00 ml (66.64 mmol) of allylamine was added to the compound, followed by stirring at room temperature for 5 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 346 mg (48.1%) of the title compound.

Provenance & Evidence