ethyl N-(2-chloro-5-nitropyrimidin-4-yl)-N-phenylalaninate → 2-chloro-7-methyl-8-phenyl-7,8-dihydropteridin-6(5H)-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl N-(2-chloro-5-nitropyrimidin-4-yl)-N-phenylalaninate (1.6 g, 4.56 mmol) in glacial acetic acid (35 mL) was added iron powder (1.6 g, 28.57 mmol). The resulting mixture was heated at 70° C. for 2 h. The insoluble material was then filtered off celite to give a clear solution. The bulk of solvent was evaporated to give a crude residue, which was purified by silica gel flash chromatography (eluent: 2% methanol in dichloromethane) to afford desired product (75%). 1HNMR (300 MHz, DMSOd6): δ 1.29 (d, J=6.6 Hz, 3H), 4.58-4.60 (m, 1H), 7.36-7.50 (m, 5H), 7.70 (s, 1H) and 10.94 (s, 1H).

Provenance & Evidence