4-Iodo-2-methoxynicotinaldehyde → HCID 178494185, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-(5-amino-4-methyl-6-nitro-pyrimidin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (3.18 g, 9.4 mmol) in methanol (200 mL) and 10% palladium on carbon (180 mg) were added methanol (10 mL) under nitrogen. The reaction mixture was stirred under hydrogen atmosphere (hydrogen balloon) for 18 hours. The solution was filtered through a pad of celite and the filtercake was washed with a small amount of MeOH. This solution was cooled to 0° C. and the 4-iodo-2-methoxy-pyridine-3-carbaldehyde (2.47 g, 9.4 mmol) in methanol (50 mL) was added to the reaction mixture and stirred at 23° C. for 18 hours. Then iodobenzene diacetate (3.03 g, 9.4 mmol) was added and the reaction mixture was stirred at 23° C. for 5 hours. MeOH was evaporated in vacuo and the crude material was purified on silica gel column using EtOAc:Hex (1:2 to 1:1 gradient) to give the title compound as a yellow solid. (2.75 g, 53%). HPLC 98%. LCMS (+ESI, M+H+) m/z 552; IR (KBr, cm−1) 3177, 2976, 1699, 1558, 1223; 1H NMR (400 MHz, DMSO) δ 12.92 (s, 1H), 8.0 (d, J=5.1 Hz, 1H), 7.64 (d, J=5.6 Hz, 1H), 3.81 (s, 3H), 3.73 (br s, 4H), 3.43 (br s, 4H), 2.57 (s, 3H), 1.44 (s, 9H).

Provenance & Evidence