Hydrogen Peroxide → 2-(4-Phenyl-butyl)-3H-pyrimido[4,5-d]pyrimidin-4-one

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Reaction Steps

Under an atmosphere of nitrogen, K2CO3 (3.057 g) was added to a solution of 5-phenyl-pentanoic acid (5-cyano-pyrimidin-4-yl)-amide (1.00 g) in MeOH (5 ml) and DMSO (1.2 ml). The mixture was cooled (ice bath) and hydrogen peroxide (35% in H2O, 1.5 ml) was added dropwise. The mixture was taken up in ethyl acetate and washed with water. The organic layer was dried (Na2SO4), filtered, and the solvent was evaporated. 2-(4-Phenyl-butyl)-3H-pyrimido[4,5-d]pyrimidin-4-one (18 mg, 1.8%) was obtained from the residue by subsequent column chromatography (silica gel, eluent gradient n-heptan/ethyl acetate=100:0-60:40) and preparative, reverse-phase HPLC (Agilent Zorbax XdB C18 column, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 7 min, flow rate 30 ml/min). MS: m/e=279.3 [M−H−]. 1H NMR (d6-DMSO): δ 1.62-2.00 (m, 4H), 2.55-2.80 (m, 4H), 7.17-7.18 (m, 2H), 7.26-7.28 (m, 3H), 9.56 (d, 1H), 9.64 (d, 1H), 11.13 (bs, 1H).

Provenance & Evidence