Introduction. Among the 5-substituted-6-hydroxy-2,3-diarylpyrimidine-4(3H)-ones derivatives, there are compounds with reported anti-inflammatory activities and analgesic activity. It is known that the pharmacological activity can vary depending on how many pyrimidine rings there are in the molecule. Various reports in the patent and scientific literature have revealed that bis(pyrimidine) derivatives exhibit antitumor and antimicrobial activity. Therefore, the aim of our work was the synthesis of new derivatives of bis(6-hydroxypyrimidin-4(3H)-one) with aromatic linker – 2,2'-(1,4-phenylene)bis(6-hydroxy-5-methyl-3-phenylpyrimidin-4(3H)-one) (1) and 3,3'-(1,4-phenylene)bis(6-hydroxy-5-methyl-2-phenylpyrimidin-4(3H)-one) (2). Proof of structure and assessment of the biological activity were conducted through in silico analysis. Methods. Сompounds 1 and 2 were obtained as a result of the interaction between methylmalonyldichloride and the corresponding carboximidamide in boiling benzene medium for 17 h. The structure of the obtained compounds was reliably proven by ¹Н and ¹³С NMR spectroscopy data. Prediction of biological activity spectra was carried out using web resources: GUSAR, PASS Online, AntiHIV-Pred и CLC Pred. Results and Conclusions. 2,2'-(1,4-phenylene)bis(6-hydroxy-5-methyl-3-phenylpyrimidin-4(3H)-one) and 3,3'-(1,4-phenylene)bis(6-hydroxy-5-methyl-2-phenylpyrimidin-4(3H)-one) were obtained in 36 % и 42 % yields, accordingly. The structure of the obtained compounds was reliably proven by ¹Н and ¹³С NMR spectroscopy data. The biological activity of the synthesized compounds was evaluated in silico, specifically, the acute toxicity and spectrum of pharmacological properties. According to the results of screening, compounds 1 and 2 potentially exhibit antitumor activity against cisplastin-resistant ovarian carcinoma and diffuse large B-cell lymphoma-activated B-cell type, antiviral activity against Dengue virus type 2 and SARS-CoV-2 with a high probability. Also, they can effectively inhibit reverse transcriptase (HIV-1). The predicted values of acute toxicity in rats (LD₅₀) with the intravenous route of administration for compounds 1 and 2 were 314 mg/kg and 309 mg/kg, accordingly, with the oral routes of administration at 1525 mg/kg and 1611 mg/kg, accordingly.