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With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -50 - 20℃; for 1.08333h;
To a stirred mixture of (69) (700 mg, 3.92 mmol), 4-nitronaphthol (2) (741 mg, 3.92 mmol) and PPh3 (1.23 g, 4.70 mmol) in THF (20 mL) under nitrogen at ?50° C. was added DIAD (996 muL, 4.70 mmol) dropwise over 5 min. The mixture was allowed to warm to RT and stirred for 1 hr during which time a yellow precipitate formed. The suspension was stirred overnight and the volatiles were evaporated in vacuo. The residue was triturated from MeOH (50 mL) and the pale yellow solid collected by filtration and washed with diethyl ether (50 mL) to give 4-((4-nitronaphthalen-1-yloxy)methyl)pyrimidin-2-amine (70) (1.10 g, 93percent): m/z 297 (M+H)+ (ES+).
With DIAD; triphenylphosphine; In tetrahydrofuran; methanol;
To a stirred mixture of (69) (700 mg, 3.92 mmol), 4-nitronaphthol (2) (741 mg, 3.92 mmol) and PPh3 (1.23 g, 4.70 mmol) in THF (20 mL) under nitrogen at -50° C. was added DIAD (996 muL, 4.70 mmol) dropwise over 5 min.The mixture was allowed to warm to RT and stirred for 1 hr during which time a yellow precipitate formed.The suspension was stirred overnight and the volatiles were evaporated in vacuo.The residue was triturated from MeOH (50 mL) and the pale yellow solid collected by filtration and washed with diethyl ether (50 mL) to give 4-((4-nitronaphthalen-1-yloxy)methyl)pyrimidin-2-amine (70) (1.10 g, 93percent): m/z 297 (M+H)+ (ES+).
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