Triethylamine → N-{4-[3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methyl-2-oxopyridin-1(2H)-yl]phenyl}-3-methyl-2-furamide

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-1-(4-aminophenyl)-4-methylpyridin-2(1H)-one (25 mg, 0.075 mmol) was dissolved in THF (2 mL) and NEt3 (3 mL) and then treated with 3-methylfuran-2-carbonyl chloride (13 mg, 0.090 mmol). The reaction was heated to 40° C. and allowed to stir for 3 h. The reaction was cooled and then extracted with EtOAc (3ט10 mL) and water (˜10 mL). The combined organic layers were then washed with ˜20 mL of NaHCO3(aq). The organic layers were then dried over anhydrous Na2SO4 (s), filtered and the concentrated in vacuo. The crude mixture was purified over silica (EtOAc/Hexanes gradient). Following concentration of the appropriate fractions the title compound was isolated as a grey solid (25 mg, 76%). 1H NMR (DMSO) δ: 9.52 (s, 1H), 7.92 (s, 1H), 7.80(m, 1H), 7.42-7.52 (m, 2H), 7.41 (m, 1H), 7.24-7.32 (m, 2H), 6.66 (m, 1H), 6.28 (s, 2H), 6.14 (m, 1H), 4.01 (br. s, H), 3.24 (s, 2H), 2.67 (t, J=5.3 Hz, 2H), 2.35 (s, 3H), 2.20 (s, 3H).

Provenance & Evidence