Cyanoacetic acid → 6-Amino-1,3-bis(cyclohexylmethyl)uracil

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Reaction Conditions

Reaction Steps

Cyanoacetic acid (Aldrich, 21.0 g, 0.247 mole) was dissolved in acetic anhydride (260 mL). This solution was added to 1,3-bis(cyclohexylmethyl)urea (from step (a), 54.5 g, 0.216 mole) and the solution maintained at 80° C. for 2 h under nitrogen. Volatiles were removed in vacuo and the residual oil dried by evaporation of portions of 10% water-ethanol (3×400 mL). The residual solids were dissolved in ethanol (600 mL)-water(300 mL) at 80° C. with adjustment of the pH to 10 by addition of 10% aqueous sodium carbonate. The hot solution was diluted with water (75 mL) and cooled to ambient temperature. The colorless crystals which formed were filtered off, washed with water (3×500 mL) and dried at 0.5 Torr to give 6-amino-1,3-bis(cyclohexylmethyl)uracil (64.98 g, 94%), m.p. 138°-141° C.;

Provenance & Evidence