Methanol → N-(5-(5-amino-2-(3-methyl-1H-1,2,4-triazol-1-yl)phenoxy)pentan-2-yl)-2-chloro-7-(2,4-difluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

Iron powder-325 mesh (0.63 g, 11.4 mmol) was added to a round bottom flask charged with a mixture of 2-chloro-7-(2,4-difluorophenyl)-N-(5-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)pentan-2-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (0.65 g, 1.14 mmol), methanol (15 mL), THF (30 mL), water (15 mL) and ammonium chloride (0.61 g, 11.4 mmol). A water-cooled reflux condenser was attached to the flask and the heterogeneous mixture was heated at 70° C. with vigorous stirring for 2 h. The reaction mixture was filtered and washed with methanol. The filtrate was concentrated in vacuo. EtOAc (250 mL) was added to the residue and was washed with brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to afford the light yellow solid N-(5-(5-amino-2-(3-methyl-1H-1,2,4-triazol-1-yl)phenoxy)pentan-2-yl)-2-chloro-7-(2,4-difluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (500 mg, 81%). LC-MS (M+H)+=540.2. 1H NMR (400 MHz, CDCl3) δ ppm 8.32 (1H, s), 7.32-7.30 (1H, m), 6.96-6.94 (1H, m), 6.81-6.75 (2H, m), 6.34-6.29 (2H, m), 4.83 (1H, br m), 4.44-4.43 (2H, m), 4.09-4.00 (2H, m), 3.77 (2H, br s), 3.13-3.12 (1H, m), 2.64-2.56 (2H, m), 2.47 (3H, s), 1.94-1.80 (3H, m), 1.63-1.61 (2H, m), 1.27-1.22 (3H, m).

Provenance & Evidence