2,5-Hexanedione → 2-[(S)-1-phenylethylamino]-4-[5-(2,5-dimethylpyrrol-1-yl)benzimidazol-1-yl]pyrimidine

Participants

Reaction Steps

2-[(S)-1-Phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidine (EXAMPLE 79) (100 mg) and acetonyl acetone(0.04 mL)and acetic acid (20 drops) were dissolved in benzene (10 mL) and refluxed with Dean-Stark apparatus for 2 hours. After cooling to room temperature, the solution was then diluted with 10 mL of aqueous saturated NaHCO3 and extracted with 2×10 mL of of EtOAc. The combined organic extracts were then dried (MgSO4) and concentrated under reduced pressure. The residue was purified with preparatory thin-layer chromatography (SiO2, 5% MeOH in CH2Cl2) to yield 17 mg of the title compound. Mass spectrum (ESI) 408.1 (M+).

Provenance & Evidence