N,N'-Dicyclohexylurea → 1,4-dihydro-4-oxo-5-(phenylmethoxy)-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridine-carboxamide

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Reaction Steps

To a solution of 4.7 g. (19.2 mmol) 1,4-dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid in 50 ml N,N-dimethylformamide was added 4.74 g (23 mmol) dicyclohexylcarbodiimide and 0.29 g (1.92 mmol) N-hydroxybenzotriazole. The mixture was stirred for 1 hour. To this was added a solution of 2.85 g (19.2 mmol) 3-aminotetrahydro-2(1H)-pyrimidinone, monohydrochloride and 1.94 g (19.2 mmol) triethylamine in 30 ml N,N-dimethylformamide. After stirring overnight the dicyclohexylurea was filtered off and the N,N-dimethylformamide evaporated in vacuo. The residue was triturated with ether to yield 8.47 g of the desired product (contained dicyclohexylurea). This crude material was used in the next step without further purification.

Provenance & Evidence