Potassium Carbonate → HCID 70091948, compound

Participants

Reaction Conditions

Reaction Steps

The ester 15-5 (400 mg, 1.38 mmol) was treated with 9-BBN (8.28 mL, 4.14 mmol; 0.5M in TBF) at room temperature for 16 hours. To this solution was added Pd(OAc)2 (31 mg, 0.14 mmol), 6-chloro-2,4-diaminopyrimidine (219 mg, 1.52 mmol), K2CO3 (381 mg, 2.75 mmol), 1,1′-bis(diphenylphosphino)-ferrocene (76 mg, 0.14 mmol) and DMF (15 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 ethanolarnine (5 mL) for 2 hours. The mixture was partitioned between 1N HCl and EtOAc. The aqueous layer was made basic with K2CO3 and extracted with EtOAc (5×). The organic layers were washed with brine, dried (MgSO4) and concentrated. Purification by silica gel chromatography (20% MeOH in CHCl3) afforded the title compound 15-6 as an oil.

Provenance & Evidence