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The next step was to explore the effect of gold nanoparticles on the reaction rate (Scheme 4). As shown in the reaction, the number of the gold nanoparticles on the PGMA colloid could affect the reaction rate. When the gold nanoparticles were on the PGMA colloid, the reaction time could be reduced and the average reaction rate could also be increased. This finding implied that PGMA colloid could support the large numbers of gold nanoparticles to reduce the reaction time and increase the average reaction rate.

The proposed reaction mechanism is presented in Scheme 3. (1) Formation of the gold-coupled pyrimidinium from pyrimidinone and gold catalysts. (2) Nucleophilic addition of 1,2-dibromoethane to the Pyrimidinium. (3) Nucleophilic addition of bromine to the Pyrimidinium. (4) Reaction between nucleophilic intermediate and gold-coupled pyrimidinium. (5) Bis-Dihydro-Pyrimidinium. (6) Rate-determining step of the catalyzed reaction, the attack of 1,2-dibromoethane by gold-coupled pyrimidinium to form bis-derivatives (S-, S-), (1N-,1N-), or (3N-, 3N-). (7) Reaction between bis-derivatives and 1,2-dibromoethane to form Pyrimidinium.

Based on the above-described reaction conditions, a series of reactions were investigated in this work. It turned out that more than 95% of the nucleophile was added to the gold-coupled pyrimidinium, and the addition was quite fast.

Next, the reaction of 6-amino-2-mercapto-3H-pyrimidin-4-one 3 with 2,2-difluoro-1-iodoethane (4b) (Scheme 3) as the model reaction was studied. The reaction was conducted in a similar manner as that of the model reaction with 1,2-dibromoethane (4a) (Scheme 2), except that, 1,2-difluoro-1-iodoethane (4b) was used. Among the solvents tested, isopropyl alcohol proved to be the most effective. The product of reaction with 5.8% (Scheme 3, entry 3) was a mixture of the symmetrical bis-derivatives (S-, S-), (1N-,1N-), or (3N-, 3N-) or the asymmetrical derivatives (S-, 1N-), (S-, 3N-) or (1N-, 3N-). Next, the stability of the product was examined (Scheme 3, entry 4), which was found to be more stable when heated at 60°C for 2 h, (25% decomposed), than at room temperature for 24 h (90.3% decomposed), as determined by TLC analysis. The tetrachloroaurate catalyst (1 mM) was much more active than the gold nanoparticles catalyst (1 mM). The gold-catalyzed reaction proceeded smoothly without the formation of any side products or by-products under the same experimental conditions, and the reaction rate depended on the type of solvent used. Further studies by other methods gave a similar result that isopropyl alcohol was the best solvent for the reaction.

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