(R)-tert-butyl 3-((4-(5-(2,6-difluorophenyl)-1H-indol-3-yl)-6-methoxypyrimidin-2-yl)amino)piperidine-1-carboxylate → (R)-6-(5-(2,6-difluorophenyl)-1H-indol-3-yl)-2-(piperidin-3-ylamino)pyrimidin-4(3H)-one

Participants

Reaction Steps

A solution of (R)-tert-butyl 3-((4-(5-(2,6-difluorophenyl)-1H-indol-3-yl)-6-methoxypyrimidin-2-yl)amino)piperidine-1-carboxylate (0.17 g, 0.318 mmol) in 33% HBr in HOAc (3 mL) was heated at 90° C. for 14 h. The reaction was quenched with aq. NaHCO3 and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was washed with 50% EtOAc in petroleum ether to give (R)-6-(5-(2,6-difluorophenyl)-1H-indol-3-yl)-2-(piperidin-3-ylamino)pyrimidin-4(3H)-one (30 mg, 22%). MS (ESI, pos. ion) m/z: 422.1 (M+1); 1H-NMR (400 MHz DMSO-d6): δ ppm 11.78 (s, 1H), 8.48 (s, 1H), 8.13 (d, J=2.4 Hz, 1H), 7.53 (d, J=8.8 Hz, 1H), 7.40-7.47 (m, 1H), 7.18-7.22 (m, 3H), 6.59 (brs, 1H), 6.00 (s, 1H), 3.93 (brs, 1H), 2.57 (s, 2H), 2.90 (d, J=9.2 Hz, 1H), 1.74 (brs, 1H), 1.50-1.53 (m, 2H), 1.18-1.22 (m, 3H).

Provenance & Evidence