Br[C:2]1[C:10]2[CH:9]=[N:8][CH:7]=[N:6][C:5]=2[N:4]([S:11]([C:14]2[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1.[CH3:21][C:22]1([CH3:29])[C:26]([CH3:28])([CH3:27])[O:25][BH:24][O:23]1.C([O-])(=O)C.[K+]>COCCOC.Cl[Pd]Cl>[CH3:21][C:22]1([CH3:29])[C:26]([CH3:28])([CH3:27])[O:25][B:24]([C:2]2[C:10]3[CH:9]=[N:8][CH:7]=[N:6][C:5]=3[N:4]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:3]=2)[O:23]1As shown in FIG. 1—step iv, a mixture of compound 1004 (140 mg, 0.40 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane dimer (121 mg, 0.477 mmol), PdCl2 dppf2 (16 mg, 0.02 mmol) and potassium acetate (117 mg, 1.19 mmol) in 2 mL of DME were microwaved at 150° C. for 10 minutes. The reaction mixture was filtered through a short pad of silica gel with 30% EtOAc-70% hexanes as eluent to provide, after concentration to dryness, 158 mg (98%) of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, compound 1005: ESMS M+1=317.07.
Wird geladen…