4-Methylmorpholine → HCID 69524860, compound

Participants

Reaction Steps

A mixture of trans-cinnamic acid (376 mg. 2.5 mmol), 2-chloro-3,5-dimethoxy-2,4,6-triazine (500 mg, 2.8 mmol), N-methylmorpholine (0.32 mL, 2.9 mmol), and tetrahydrofuran (20 mL) was stirred without cooling for 1.5 hours. Compound (XI) (1.0 g, 2.5 mmol) was added, then the reaction was stirred for an additional 18 hours. The solvent was evaporated, and the residue was dissolved in ethyl acetate, washed once with 1N hydrochloric acid, once with saturated sodium bicarbonate solution, dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 30% ethyl acetate: 70% hexanes) of the residue provided 800 mg (61%) of Example 11 as a solid: mp 114–117° C.

Provenance & Evidence