Nitric Acid → 2-(2-Ethoxy-5-nitrophenyl)-8-n-propylpyrido[3,2-d]pyrimidin-4(3H)-one

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A solution of 2-(2-ethoxyphenyl)-8-n-propylpyrido-[3,2-d]pyrimidin-4(3H)-one (Preparation 8; 0.80 g, 0.0026 mol) in a mixture of concentrated sulphuric acid (5.4 ml) and concentrated nitric acid (0.20 ml) was stirred at ambient temperature for 4.5 hours. The mixture was then poured cautiously into stirred ice/water (50 g) and the resulting mixture extracted with a methanol:dichloromethane mixture (1:9, 3×50 ml). The organic extracts were combined, dried (MgSO4) and evaporated under vacuum, and the residue crystallised from ethyl acetate:methanol to give the title compound as an off-white solid (0.71 g, 77%), m.p.257°-259° C. Found: C,61.28; H,5.11; N,15.60. C18H18N4O4 requires C,61.01; H,5.12; N,15.81%.

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