Water → HCID 86629444, compound

Participants

Reaction Steps

To suspension 2-chloro-5-((4-fluoro-2-methyl-5-nitrophenylamino)methyl)-N-methylpyridin-4-amine (2.04 g, 6.28 mmol) in dioxane (30 mL) was added Et3N (3.50 mL, 25 mmol) and phosgene (20% solution in toluene, 6.90 mL, 12.6 mmol). The reaction mixture was stirred at RT for 2.5 h. Water 30 mL) was added and the mixture was extracted with EtOAc (2×70 mL). The combined organics were washed with brine (15 mL), dried (MgSO4) and concentrated in vacuo. The residue was stirred with EtOAC for 15 min and the precipitate was collected by filtration and dried in vacuo to give 7-chloro-3-(4-fluoro-2-methyl-5-nitrophenyl)-1-methyl-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (0.785 g, 36% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.31 (s, 1H), 8.11 (s, 1H), 7.61 (s, 1H), 7.15 (s, 1H), 4.94 (s, 1H), 4.61 (s, 1H), 3.26 (s, 3H), 2.22 (s, 3H); MS (ESI) m/z: 351.0 [M+H+].

Provenance & Evidence