Dimethylformamide → Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-formyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

Ethyl 1-[5-[7-bromo-2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (Intermediate 9) (2.58 g, 4.28 mmol) was dissolved in DMF (50 mL). Triethylamine (1.19 mL, 8.56 mmol), 1,3-bis(diphenylphosphino)propane (200 mg, 0.4 mmol), triethylsilane (2.05 mL, 12.8 mmol), Pd(OAc)2 (100 mg, 0.4 mmol) and Pd(dppf)Cl2DCM (200 mg, 0.2 mmol) were added and the mixture stirred at 75° C. for 32 h under an atmosphere of carbon monoxide (160 psi). The reaction mixture was cooled to rt, concentrated to dryness and the solid residue purified by flash column chromatography (80 g GraceResolv silica cartridge—dry loaded) eluting with 0-20% MeOH/CH2Cl2 to afford a brown solid. This solid was washed with EtOAc to afford the desired compound (690 mg, 29%) as an off-white solid. MS: 552.08 [M+H]+.

Provenance & Evidence