The mixture of 4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butan-1-amine, 2 TFA (46.6 mg, 0.090 mmol), 2,4-dichloro-8-(4-fluorophenyl)-6-methyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (20 mg, 0.064 mmol) and DIEA (55.9 μL, 0.320 mmol) in acetonitrile (320 μL) and 2 drops of MeOH was stirred at rt overnight. The crude product was purified by Prep-HPLC to obtain 2-chloro-8-(4-fluorophenyl)-6-methyl-N-(4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine, 2 TFA (43.6 mg, 82% yield). LC-MS (M+H)+=567.2. 1H NMR (500 MHz, methanol-d4) δ 9.00 (s, 1H), 8.06 (d, J=2.1 Hz, 1H), 8.03-7.95 (m, 2H), 7.21-7.12 (m, 2H), 7.04-6.96 (m, 2H), 4.39 (t, J=6.3 Hz, 2H), 4.00 (s, 1H), 3.60-3.52 (m, 2H), 3.42-3.23 (m, 2H), 2.94 (dd, J=11.7, 5.4 Hz, 1H), 2.68 (dd, J=11.7, 6.0 Hz, 1H), 2.48-2.39 (m, 6H), 1.99 (t, J=6.8 Hz, 2H), 1.84 (td, J=7.2, 3.4 Hz, 2H).
