2-Propenoic acid, 3-(4-formylphenyl)- → HCID 178525292, compound

Participants

Reaction Steps

In the manner of step (d) of example 8, 6-amino-1,3-bis(cyclohexylmethyl-1,2-dihydro-5-nitroso-2-thioxo-4(3H)-pyrimidinone (from step (c), 3.00 g, 8.20 mmol) was reduced to 1,3-bis(cyclohexylmethyl)-5,6-diamino-1,2-dihydro-2-thioxo-4(3H)-pyrimidinone, which was then combined with 4-formylcinnamic acid (Aldrich, 1.44 g, 8.20 mmol) in ethanol (150 mL). The resulting yellow mixture was dried by evaporation of several portions of absolute ethanol, and the residual yellow powder (Schiff base intermediate) was heated at reflux in nitrobenzene (150 mL) until no more water distilled off. The reaction mixture was then cooled to ambient temperature, and stirred in ether (200 ml). The resulting pale yellow precipitate was filtered off, washed with hot ethanol (100 mL), followed by ether (100 mL), and dried under vacuum at 110° C. to afford (E)-4-(1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-6-oxo-2-thioxo-9H-purin-8-yl)cinnamic acid as a yellow powder (2.32 g, 65%), m.p. >300° C.; 1H-NMR (DMSO-d6) consistent with structure.

Provenance & Evidence