Synthesis of New Quinazoline-2,4(1 H,3 H )-dione non-nucleoside Analogues of the reverse transcriptase inhibitor TNK-651

The synthesis is described of a series of new non-nucleoside analogues of the reverse transcriptase inhibitor TNK-651 from quinazoline-2,4(1H,3H)-diones. Compounds 2a–c were silylated and treated with benzyl chloromethyl ether in the presence of CsI to give 1-benzyloxymethylquinazoline derivatives 3a–c. Treatment of the silylated quinazolinediones 2a–c with the appropriate acetals 5a–e in the presence of TMS triflate afforded the corresponding TNK-651 analogues 6–10.