[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(C1C=CC=CC=1NC(=O)C1C=CC=CN=1)#N.[C:34]([C:38]1[CH:43]=[C:42](I)[CH:41]=[C:40]([I:45])[C:39]=1[O:46][CH3:47])([CH3:37])([CH3:36])[CH3:35]>CS(C)=O.[Cu]I.CC#N>[C:34]([C:38]1[CH:43]=[C:42]([N:1]2[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]2=[O:3])[CH:41]=[C:40]([I:45])[C:39]=1[O:46][CH3:47])([CH3:37])([CH3:35])[CH3:36]
Uracil (33.3 g, 297 mmol, 1.2 equiv.), K3PO4 (106 g, 500 mmol, 2.1 equiv.), CuI (4.6 g, 24.2 mmol, 0.1 equiv.), and N-(2-cyanophenyl)picolinamide (6.4 g, 28.7 mmol, 0.12 equiv.) were charged to a flask and inerted with argon. The 1-tert-butyl-3,5-diiodo-2-methoxybenzene was solvent switched into MeCN, dissolved in 1 L DMSO and sparged with argon and added to the solids. The reaction was heated to 60° C. for 16 h. After cooling, the reaction was diluted with 2 L EtOAc and washed with 2.6 L water (back extracted with 3×1 L EtOAc). The combined organic layers were washed with 2×1 L of 0.25M (CuOAc)2 then 2×830 mL 15% NH4Cl then 800 mL brine. The organic layer was then concentrated and chased with 1 L heptane, then triturated with refluxing 85:15 (v/v) heptane:iPrOAc for 4 h. After cooling, the product was collected by filtration and washed with an additional 330 mL of 85:15 v/v heptanes:EtOAc to yield after drying 66.9 g (70% yield) of the product as a white solid.
読み込み中…
