Morpholine → 3-Bromo-8-(4-morpholinyl)pyrido[2,3-d]pyridazine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromopyrido[2,3-d]pyridazin-8(7H)-one (0.206 g, 0.91 mmol) and phosphorus oxychloride (5.00 ml, 55 mmol) was heated at 95° C. After 2 h the reaction was cooled to 25° C. and diluted with 30 mL of CHCl3. The solution was cooled to 0° C. and the solid was filtered and washed with CHCl3. The filtrate was concentrated to dryness and azeotroped with toluene (2×). The residue was dissolved in CH3CN and heated with morpholine (0.079 ml, 0.91 mmol) at 190° C. for 15 min in the microwave. The crude material was purified by flash chromatography eluting with 2M NH3 in MeOH:CH2Cl2 (0:1→1:24) to give the title compound as an orange amorphous solid. MS m/z: 295.0 [M+1].

Provenance & Evidence