Triethylamine → HCID 53682266, compound

Participants

Reaction Steps

To a stirred suspension of 3,4-dihydro-2,5,7,8-tetramethyl-2-(1-piperazinylmethyl)-2H-1-benzopyran-6-ol (EXAMPLE 126, 0.7 g), triethylamine (0.23 g, 2.3 mmol) and THF (10 ml), cooled to 0° in an ice-water bath, is added in a steady stream 4,6-dichloropyrimidine in THF (5 ml). The cooling bath is removed and the mixture stirred at 20°-25° for 18 hr. Ethyl acetate (50 ml) is added and the mixture is washed with water (50 ml), saline, dried over sodium sulfate and the solvent removed at reduced pressure to leave a residue that is dissolved in pyrrolidine (5 ml). The mixture is heated at reflux for 2 hr and concentrated at reduced pressure. The residue is flashed chromatographed on silica gel (50 g) eluting with ammonia, methanol and ethyl acetate (0.5/4.5/95) to give the product which is crystallized from hexane-ethyl acetate to give the title compound.

Provenance & Evidence