Potassium Carbonate → 6-Amino-7-cyclopropyl-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-amino-7-bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.500 g, 1.607 mmol), cyclopropylboronic acid (1.38 g, 16.07 mmol), K2CO3 (0.888 g, 6.43 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.262 g, 0.321 mmol) in water (10 mL) and dioxane (60 mL) was heated at 130° C. for 2 h. The reaction mixture was cooled to ambient temperature and the solution was concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 30-100% EtOAc in petroleum ether) to give 6-amino-7-cyclopropyl-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.235 g, 0.863 mmol, 54%). 1H NMR (DMSO-d6, 400 MHz): δ 10.71 (s 1H), 6.50 (s, 1H), 6.45 (s, 1H), 4.75 (brs, 2H), 4.45 (m, 3H), 1.60 (m, 1H), 1.31 (d, J=6.8 Hz, 3H), 0.83 (m, 2H), 0.46 (m, 2H).

Provenance & Evidence