Potassium Carbonate → HCID 69667060, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 4-pentenoate (1.0 g, 7.8 mmol) was treated with 9-BBN (18.72 mL, 9.36 mmol; 0.5M in THF) at room temperature for 16 hours. To this solution was added Pd(OAc)2 (175 mg, 0.78 mmol), pyrimidine 7-2 (2.44 mg, 7.8 mmol), K2CO3 (2.15 g, 15.6 mmol), 1,1′-bis(diphenylphosphino)-ferrocene (DPPF) (433 mg, 0.78 mmol) and DMF (25 mL). The mixture was degassed with argon for 10 minutes then heated to 80° C. for 24 hours. The reaction mixture was cooled and stirred with ethanolamine (10 mL) for 3 hours. The mixture was partitioned between saturated NaHCO3 and EtOAc, washed with brine, dried (MgSO4) and concentrated. Purification by silica gel chromatography (hexane:EtOAc 2:1) afforded the title compound 7-3 as a solid.

Provenance & Evidence