HCID 70124084, compound → HCID 20703633, compound

Participants

Reaction Steps

A solution of 2-[1-(1-(benzyloxycarbonyl)-4-(tert-butyloxycarbonyl)-piperazin-2-yl)-ethylamino]-4-(benzimidazol-1-yl)-pyrimidine (EXAMPLE 14, Step E; 30 mg) in 3 mL of MeOH was stirred over Pd(OH)2/C (30 mg) under an H2 atmosphere (balloon) for 4 h, then filtered through Celite®, washing liberally with MeOH, and concentrated. The residue was dissolved in 1 mL of MeOH and NaBH3CN (6.8 mg) and 37% aqueous formaldehyde (26 μL) were added and the mixture was stirred for 5 h at room temperature, then diluted with 5 mL of EtOAc and poured into 10 mL of water. The phases were separated and the aqueous phase was extracted with 2×5 mL of EtOAc. The aqueous phase was basified (pH>10) by addition of 5N NaOH, then extracted with 5×5 mL of EtOAc. The combined organic extracts were washed with 5 mL of brine, dried over Na2SO4, and concentrated. The residue (16 mg) was dissolved in 1 mL of CH2Cl2 and 0.5 mL of trifluoroacetic acid was added. The mixture was stirred for 1 h at room temperature, then poured into 10 mL of water and extracted with 2×5 mL of CH2Cl2. The aqueous phase was basified (pH>10) by addition of 5N NaOH, then extracted with 4×5 mL of EtOAc. The combined organic extracts were washed with 5 mL of brine, dried over Na2SO4, and concentrated. The residue was purified by preparative thin-layer chromatography, eluting with 9:1 CH2Cl2—2M NH3 in MeOH to provide 9.4 mg of the title compound. Mass spectrum (ESI) 338.3 (M+1).

Provenance & Evidence