Trifluoroacetic acid → 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-1-(4-aminophenyl)-4-methylpyridin-2(1H)-one

Participants

Reaction Steps

Tert-butyl (4-(5-(2-amino-7,8-dihydropyrido[4,3-d]p yrimidin-6(5H)-yl)-4-methyl-6-oxo-5,6-dihydropyridin-1(2H)-yl)phenyl)carbamate (150 mg, 0.334 mmol) was dissolved into a 1:1 mixture of MeOH/THF (˜10 mL) and treated with CF3COOH drop wise and the reaction was allowed to stir for 4 h. One the reaction was completed, the residual CF3COOH was neutralized with NaHCO3 (aq). The reaction was then extracted with EtOAc (3×10 mL) and brine (˜10 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and then concentrated in vacuo. The crude organic oil was then purified via column chromatography (MeOH/CHCl3 gradient). Concentration of the appropriate fractions provided the title compound (102 mg, 88%). 1H NMR (DMSO) δ: 7.92 (s, 1H), 7.45-7.52 (m, 2H), 7.41 (d, J=6.7 Hz, 1H), 7.24-7.31 (m, 2H), 6.28 (s, 2H), 6.17 (d, J=7.0 Hz, 1H), 3.96 (br. S, H), 3.29 (s, 2H), 2.66 (t, j=5.3 Hz, 2H), 2.18 (s, 3H).

Provenance & Evidence