Picolinic acid → US9296747, Example 15

Participants

Reaction Steps

A mixture of 2-picolinic acid (40.6 mg, 0.33 mmol), N, N-diisopropylethylamine (0.105 mL, 0.60 mmol), and HBTU (125 mg, 0.33 mmol) in DMF (2.0 mL) was stirred at room temperature for 5 minutes, then N-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine, Intermediate 1 (94.8 mg, 0.30 mmol; see Syntheses of Starting Materials section for prep) added and the reaction continued for 1.5 hours at rt. The reaction mixture was treated with an EtOAc/aqueous Na2CO3(aq) solution work-up to give an orange oil. The oil was chromatographed eluting with 5% MeOH in 1:1 EtOAc/CHCl3 giving an off-white solid (107 mg, 85%).

Provenance & Evidence