Triethylamine → Pyrido[2,3-d]pyrimidine

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Reaction Steps

Those compounds of the present invention where R2 is prop-1,3-diyl are prepared by first preparing a benzoic acid derivative described above having a p-propen-1-yl group using the oxazoline described in Meyers, Acc. Chem. Res., 14, 375 (1978), which is incorporated herein by reference. Acid hydrolysis (5N HCl, reflux, 36 hours) affords 4-allylbenzoic acid which is converted to the corresponding diethyl-L-glutamate derivative by initial treatment with thionyl chloride (4.0 eqv., benzene, reflux, 4 hours) followed by diethyl-L-glutamate hydrochloride (2.1 equivalents), 4-dimethylamino-pyridine (0.01 eqv.) and triethylamine (18 hours). Coupling to either the pyrrolo- or pyrido[2,3-d]pyrimidine, at least by Alternative 2, affords the compounds of the present invention where R2 is a propen-1,3-diyl.

Provenance & Evidence