5-Fluorouracil → 1-(2, 4-Dimethoxycyclohexylcarbamoyl)-5-fluorouracil

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Reaction Steps

The 2, 4-dimethoxycyclohexylamine reduced from 2, 4-dimethoxyaniline by hydrogen at 110 atmospheres over a ruthenium oxide catalyst in methanol was treated with phosgene and 2, 4-dimethoxycyclohexylisocyanate was synthesized. This isocyanate, 9.2 g, was allowed to react with 6.8 g of 5-fluorouracil in 30 ml of pyridine at 90° C. for 2 hr. After evaporating the pyridine, the residue was chromatographed on silica gel and two kinds of isomers, 3.2 and 2.8 g respectively, of 1-(2, 4-dimethoxycyclohexylcarbamoyl)-5-fluorouracil were obtained. Their melting points were 122°-125° C. (Compound No. 10) and 128°-130° C. (Compound No. 11), respectively. NMR: 0.7-2.50 (6H b CH2) 2.65 (H s NHCH) 3.58 (6H s OCH3) 4.10-4.51 (H s CHOCH3) 8.38 (H d C6 --H) 9.50 (H d NHCO) 12.25 (H b N3 --H).

Provenance & Evidence