HCID 59465209, compound → HCID 25158767, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2-[(2-amino-6-chloro-5-nitro-pyrimidin-4-yl)-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)methyl]amino]acetate (Intermediate 25)(2.0 g) was dissolved in acetic acid (120 mL) and warmed to 65° C. Iron powder (5 g) was added and the mix heated at 85° C. for 40 minutes. The reaction mixture allowed to cool, filtered and the filtrate was evaporated to dryness. The residue was purified by flash chromatography on silica, eluting with increasingly polar mixtures of methanol DCM (1/99-10/90) to give crude product. The crude product was triturated with methanol (3 mL) and the resulting solid filtered off then redissolved in 5N aqueous HCl (5 mL) and heated at 80° C. for 30 minutes. The reaction mixture was cooled, evaporated to dryness and the residue triturated with aqueous ammonia solution (d=0.880). The resulting solid was filtered off to give the title compound (129 mg) as a beige coloured solid; 1H NMR spectrum (400 MHz, DMSO) 2.20 (6H, s), 3.74 (3H, s), 4.05 (2H, s), 4.79 (2H, s), 6.17 (2H, s), 8.15 (1H, s), 9.92 (1H, s);

Provenance & Evidence