[NH2:1][C:2]1[C:3]2[N:10]=[C:9](Br)[N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]3[OH:14])[C:4]=2[N:5]=[N:6][N:7]=1.[CH:21]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C[Al](C)C>C[Si](C)(C)N[Si](C)(C)C.C1COCC1.Cl[Pd]Cl>[NH2:1][C:2]1[C:3]2[N:10]=[C:9]([CH3:21])[N:8]([C@@H:12]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]3[OH:14])[C:4]=2[N:5]=[N:6][N:7]=1The compound from Step A (112 mg, 0.3 mmol) was heated at reflux in hexamethyldisilazane (15 mL) for 16 hours. The mixture was evaporated to dryness to give a syrup which was dissolved in dry THF (12 mL). PPh3 (10 mg; 0.04 mmol), PdCl2 (3.5 mg; 0.02 mmol) and AlMe3 (100 μl; 0.94 mmol) were added. The mixture was reflux for 5 hours. The mixture was evaporated to dryness. The crude product was dissolved in methanol (30 mL) in the presence of ammonium chloride. The mixture was evaporated to dryness and the residue was purified on silica gel reverse-phase (C18) using water/acetonitrile (from 9/1 to 6/4) as eluant to give the title compound (35 mg) as a yellow powder.
Loading…
