Methanol → 5,10-Dihydroxy-2,7-bis(hydroxymethyl)-3,8-dimethylpyrimido[4,5-g]quinazoline-4,9-dione

Participants

Reaction Steps

To 172 mg 10.441 mmol) of 15, suspended in 50 mL of dry benzene, was added an excess of 99% BBr, (up to 10 fold excess). The resulting mixture was refluxed for 7 hours. After cooling the reaction mixture to room temperature, methanol was added to quench the reaction. The solvent was evaporated off in vacuo and the product purified by rinsing successively with water and methanol and then dried: 106.5 mg (72%) yield; dec pt >245° C. IR (KBr pellet) 3384, 1645, 1618, 1443, 1430, 1379, 1325, 1209, 1079, 965, 793 cm-1 ; 1H NMR (dimethyl-d6 sulfoxide) 11.86 (2H, s, 5- and 10-hydroxyls), 4.62 (4H, s, methylenes), 3.61 (6H, s, 3- and 8- methyls); mass spectrum (EI model m/z 334 (P+).

Provenance & Evidence