Add time:07/21/2019         Source:sciencedirect.com

Publisher SummaryThe pyrimidine entity is one of the most prominent structures found in nucleic acid chemistry. Pyrimidine derivatives including uracil, thymine, cytosine, adenine, and guanine are fundamental building blocks for deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). Vitamin B1 (thiamine) is a well-known example of a naturally occurring pyrimidine that is encountered in our daily lives. Synthetic pyrimidine-containing compounds also occupy a prominent place in the pharmaceutical arena. Pyrimethamine and Trimethoprim are two representative pyrimidine-containing chemotherapeutics. Pyrimethamine is a dihydrofolate reductase inhibitor; effective for toxoplasmosis in combinationwith a sulfonamide; whereas Trimethoprim is an antimalarial drug, widely used as a general systemic antibacterial agent in combination with sulfamethoxazole. Due to the electronegativity of the two nitrogen atoms, the pyrimidine ring is a deactivated, π-electron-deficient heterocycle. Its chemical behavior is comparable to that of 1,3-dinitrobenzene or 3-nitropyridine. One or more electron-donating substituents on the pyrimidine ring are often required for effecting electrophilic substitution reactions. In contrast, nucleophilic displacement is significantly more facile on a pyrimidine ring compared to a pyridine ring. This trend also extends to palladium chemistry: Pd(0) undergoes oxidative addition more readily with 4-chloropyrimidine than with 2-chloropyridine.

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