Morpholine → 4-(6-Nitropyridin-3-yl)morpholine

Participants

Reaction Steps

5-Morpholin-4-yl-pyridin-2-ylamine was prepared by adapting he procedure described in J. Med. Chem., 2005, 48(7), 2388-2406. Briefly, 5-bromo-2-nitro-pyridine was reacted with morpholine and potassium carbonate in DMSO at 60-70° C. to afford 4-(6-nitro-pyridin-3-yl)-morpholine in 84% yield. Reduction with palladium on carbon under a hydrogen atmosphere provided 5-morpholin-4-yl-pyridin-2-ylamine in 70% yield. This was converted into 3-hydroxy-7-morpholin-4-yl-4-oxo-4H-pyrido[1,2-α]pyrimidine-2-carboxylic acid methyl ester in 25% yield by adapting the procedure described in Example 2, where glacial acetic acid was used instead of p-toluenesulphonic acid.

Provenance & Evidence