Diisopropylethylamine → 6-isonicotinoyl-N-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Participants

Reaction Steps

To a mixture of N-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine, Intermediate 1 (94.8 mg, 0.30 mmol) and isonicotinoyl chloride hydrochloride (56.1 mg, 0.32 mmol) in THF (2.0 mL) at room temperature was added N,N-diisopropylethylamine (0.157 mL, 0.90 mmol). After stirring for 3 hours at room temperature, an additional 21 mg of isonicotinoyl chloride hydrochloride was added and the reaction continued for 17 hours. The reaction was quenched with H2O, then treated with an EtOAc/saturated NaHCO3(aq) solution work-up to give an off-white solid. The solid was recrystallized from EtOAc/hexane to afford a white solid (115 mg, 91%).

Provenance & Evidence