Preparation of pyrimidine and pyrimidinone derivatives and their use for the treatment of HIV infections

Title compds. I and II [R1 and R2 independently = H, Et, Me, allyl, etc.; R3 = H, (un)substituted aryl or aryl-alkyl; X= H, I, Cl, Br, etc.; R6 = NR4R5 or Y-R7, wherein R4 and R5 independently = H, Me, Et, allyl, etc.; R4 and R5 may join together with N to form a (un)satd. heterocyclyl ring; R7 = Me, Et, cyclopentyl, cyclohexyl, etc.; Y = S, SO or SO2; R8 = -(CH2)2-, =O, =CH2 or =NH; R9 = Me, -(CH2)2-, =O, =CH2 or =NH], and their pharmaceutically acceptable salts, are prepd. and disclosed for the treatment of HIV infections. Thus, e.g., III was prepd. via chlorination and tosylation of 6-(2-hydroxyethyl)-2-(methylthio)-4(3H)-pyrimidinone, then reaction with dimethylamine followed by dehydration and sulfur oxidn. Select compds. of the invention were evaluated for their inhibitory activity against the reverse transcriptase of HIV-1 in the cell or enzyme test, e.g., III proved to be the most active compd. with ID50 value of 28 μM on the mutant K103N.