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

A solution of tert-butyl (4-(5-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methyl-6-oxo-5,6-dihydropyridin-1(2H)-yl)phenyl)carbamate (112 mg, 0.334 mmol) in a 1:1 mixture of MeOH/THF (˜10 mL) was treated dropwise with CF3COOH 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 (3ט10 mL) and brine (˜10 mL). The combined organic layers were dried over anhydrous Na2SO4 (s), filtered and the concentrated in vacuo. The crude organic oil was then purified via column chromatography (MeOH/CHCl3 gradient). Following concentration of the appropriate fractions the title compound was isolated (112 mg, 88%). 1H NMR (DMSO) δ: 7.91 (s, 1H), 7.80(m, 1H), 7.41-7.52 (m, 2H), 7.41 (m, 1H), 7.26-7.32 (m, 2H), 6.65(m, 1H), 6.23 (s, 2H), 6.14 (m, 1H), 4.00 (br. s, H), 3.24 (s, 2H), 2.67 (t, J=5.3 Hz, 2H), 2.34 (s, 3H), 2.22 (s, 3H).

Provenance & Evidence