Reaction SMILES: Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([CH3:15])([CH3:14])[O:12][C:11]([NH:16][C@H:17]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:18][CH2:19][O:20][Si](C(C)(C)C)(C)C)=[N:10][S:9]2(=[O:35])=[O:34])[CH:5]=[CH:6][CH:7]=1.[N:36]1[CH:41]=[C:40](B(O)O)[CH:39]=[N:38][CH:37]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.C1C=CC([C-]2C(C3C=CC=CC=3)=C(C3C=CC=CC=3)C(C3C=CC=CC=3)=C2C2C=CC=CC=2)=CC=1.[Fe+2]>[CH3:14][C:13]1([CH3:15])[O:12][C:11]([NH:16][C@H:17]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:18][CH2:19][OH:20])=[N:10][S:9](=[O:34])(=[O:35])[CH:8]1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:40]2[CH:41]=[N:36][CH:37]=[N:38][CH:39]=2)[CH:3]=1
Reactant: OB(O)c1cncnc1
Reactant: CC1(C)OC(N[C@@H](CCO[Si](C)(C)C(C)(C)C)c2ccccc2)=NS(=O)(=O)C1c1cccc(Br)c1
Agent: [Fe+2]
Agent: [Pd]
Agent: CC(C)(C)P(c1ccc[cH-]1)C(C)(C)C
Solvent: O
Solvent: Cc1ccccc1
Product: CC1(C)OC(N[C@@H](CCO)c2ccccc2)=NS(=O)(=O)C1c1cccc(-c2cncnc2)c1
Temperature: 80 °C
Reaction time: 1.5 h
Yield: 19.6 %

Procedure:
Under inert gas, a suspension of 100 mg of [5-(3-bromophenyl)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-1,4,3-oxathiazin-2-yl]-[(S)-3-(tert-butyldimethylsilanyloxy)-1-phenylpropyl]amine, 31 mg of pyrimidine-5-boronic acid and 110 mg of potassium phosphate in 2 ml of toluene was initially charged. After the addition of 10 mg of bis(dibenzylideneacetone)palladium and 24 mg of 1,2,3,4,5-pentaphenyl-1-(di-tert-butylphosphino)ferrocene, the reaction mixture was stirred at 80° C. for 1.5 h. The progress of the reaction was checked by LCMS. Since no conversion had taken place yet, 0.8 ml of water, 73 mg of potassium phosphate, 24 mg of pyrimidine-5-boronic acid, 10 mg of bis(dibenzylideneacetone)palladium and 24 mg of 1,2,3,4,5-pentaphenyl-1-(di-tert-butylphosphino)ferrocene were added and the mixture was stirred at constant temperature for a further 20 hours. After the removal of the solvent under reduced pressure, the residue was dissolved in 2 ml of methanol and 0.2 ml of concentrated hydrochloric acid, and the mixture was stirred at room temperature for 1.5 hours. The reaction solution was diluted with 20 ml of ethyl acetate and 10 ml of water, and the organic phase was washed once again with saturated aqueous sodium chloride solution, dried over MgSO4 and concentrated by rotary evaporation. The residue was purified by means of normal phase chromatography using a Flashmaster with a dichloromethane/methanol gradient. The product-containing fractions were combined and concentrated by rotary evaporation. The crude product was purified further in a purification laboratory by means of preparative HPLC. The product-containing fractions were combined, the acetonitrile was removed under reduced pressure, and the aqueous residue was basified with saturated aqueous sodium hydrogencarbonate solution and extracted with dichloromethane. The organic phase was dried over MgSO4 and concentrated by rotary evaporation, and the residue was taken up again in a mixture of acetonitrile and water and lyophilized. This gave the product (15.7 mg) with a molecular weight of 466.6 g/mol (C24H26N4O4S); MS (ESI): m/e=467 (M+H+).