Ethyl Acetate → HCID 9910299, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[(S)-1-phenylethylamino]-4-[5-iodobenzimidazol-1-yl]pyrimidine (EXAMPLE 271) (66 mg), K2CO3 (103 mg), 3-thiopheneboronic acid (58 mg) and Pd(PPh3)2Cl2 (1 mg) in anisole (6 mL) was stirred overnight at 100° C. under 1 Atm CO. The reaction mixture was poured into a separatory funnel containing 100 mL ethyl acetate and was washed with water and brine. The organic extracts were combined, dried over anhydrous MgSO4, filtered and concentrated. The product was purified by silica gel chromatography (eluted with a gradient of 100% CH2Cl2 going to 5% MeOH in CH2Cl2) followed by reverse phase chromatography (eluted with a gradient going from 50% water in methanol (with 0.1% TFA) to 100% methanol (with 0.1% TFA)). The resulting salt was then subjected to preparative thin layer chromatography (eluted with 5% (2N NH3 in MeOH) in CH2Cl2) to give 6.9 mg of the title compound. Mass spectrum (ESI): 426.0 (M+1).

Provenance & Evidence