8-Amino-2-iodo-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester → 8-Amino-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-amino-2-iodo-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester N1 (0.62 mmol) in DMF (5 mL) and under argon, HCOONa (1.4 mmol) and Pd(Ph3P)4 (0.04 mmol) were added and the mixture was heated at 100° C. for 4 h. The mixture was cooled to rt, diluted with dichloromethane and washed with water. The organic phase was dried (Na2SO4) and evaporated to dryness. Chromatography on silica gel (eluant: AcOEt/hexane 1:1) afforded the title compound (83% yield). ESI (+) MS: m/z 273 (MH+). 1H NMR: 1.32 (t, J=7.07, 3H), 2.70 (t, J=7.70, 2H), 2.90 (t, J=7.70, 2H), 4.18 (s, 3H), 4.25 (q, J=7.07, 2H), 6.35 (bs, 2H), 7.73 (s, 1H), 8.01 (s, 1H).

Provenance & Evidence