2-amino-6-(4-fluoro-3-nitrophenyl)-8-isopropylpyrido[2,3-d]pyrimidin-7(8H)-one → 2-amino-6-(3-amino-4-fluorophenyl)-8-isopropylpyrido[2,3-d]pyrimidin-7(8H)-one

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To a solution of 2-amino-6-(4-fluoro-3-nitrophenyl)-8-isopropylpyrido[2,3-d]pyrimidin-7(8H)-one (0.52 g, 1.5 mmol) in EtOAc and methanol (5:1, 30 mL) was added palladium on carbon (50 mg of 10% mol) and mixture was stirred under a hydrogen atmosphere at RT for 16 h. The mixture was filtered over a Celite pad and the pad was washed with EtOAc (2×10 mL). The combined filtrate was concentrated in vacuo to provide crude product. Purification by silica gel chromatography afforded 2-amino-6-(3-ammo-4-fluorophenyl)-8-isopropylpyrido[2,3-d]pyrimidin-7(8H)-one as an off-white solid (0.34 g, 72% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.60 (s, 1H), 7.73 (s, 1H), 7.22 (s, 2H), 7.08 (dd, J=9.2 Hz, 1.2 Hz, 1H), 6.99 (dd, J=10.8 Hz, 8.4 Hz, 1H), 6.74-6.70 (m, 1H), 5.78-5.76 (m, 1H), 5.13 (s, 2H), 1.53 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 314.0 (M+H+).

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