Formaldehyde → 2-[1-(1-Methyl-4-(tert-butyloxycarbonyl)piperazine-2-yl)-ethylamino]-4-[benzimidazol-1-yl]-pyrimidine

Participants

Reaction Steps

To a solution of 2-[1-(4-(tert-butyloxycarbonyl)piperazine-2-yl)-ethylamino]-4-(benzimidazol-1-yl)-pyrimidine (EXAMPLE 17, Step C; 17 mg) in 1 mL of MeOH and 1 mL of CH3CN was added NaBH3CN (5 mg) and 37% aqueous formaldehyde (20 μL). The mixture was stirred overnight 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 5 N 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 to yield 15 mg of the title compound.

Provenance & Evidence