3-Methyl-2-furoic acid → HCID 178497206, compound

Participants

Reaction Steps

A mixture of 3-methyl-furan-2-carboxylic acid (1.9 mg, 0.012 mmol), N,N-diisopropylethylamine (0.0064 mL, 0.037 mmol), and BOP (5.7 mg, 0.013 mmol) in 0.35 mL DMF was stirred at rt for 20 minutes, then methyl 3-[4-(methylamino)phenyl]-6-oxo-3,4,6,7-tetrahydro-2H-pyrimido[1,2-c]quinazoline-9-carboxylate (3.7 mg, 0.010 mmol) added and the reaction continued at rt. After 19 hours, the reaction was heated at 60° C. for 23 hours, then added a small spatula tip of 3-methyl-furan-2-carboxylic acid and BOP plus 0.015 mL N,N-diisopropylethylamine and continued heating at 80° C. for an additional 4 hours. The reaction mixture was partitioned between EtOAc and aqueous Na2CO3 solution, the EtOAc layer washed with H2O, brine, dried with anhydrous Na2SO4 and evaporated. The resulting yellow oil was chromatographed on a prep plate eluting with 20% MeOH/CHCl3 plus NH4OH. The obtained oily solid was then triturated with EtOAc/hexane to give the title compound as an off-white solid (1.6 mg, 31%). 1H NMR (CD3OD/CDCl3 mixture) δ: 8.14 (d, J=8.2 Hz, 1H), 7.76 (dd, J=8.2, 1.5 Hz, 1H), 7.69 (d, J=0.9 Hz, 1H), 7.41 (d, J=7.9 Hz, 2H), 7.28 (d, J=8.5 Hz, 2H), 4.49 (dt, J=12.6, 3.7 Hz, 1H), 3.96 (s, 4H), 3.66-3.76 (m, 2H), 3.28 (s, 3H), 3.17-3.24 (m, 1H), 3.05 (br. s, 2H), 2.92 (br. s, 4H), 2.62 (br. s, 7H).

Provenance & Evidence