Stannous chloride dihydrate → HCID 68181739, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-N-(5-bromo-4-fluoro-2-nitrophenyl)pyrimidine-2,4-diamine (713 mg, 2.17 mmol) in ethanol (30 mL) was added tin(II) chloride dihydrate (1.72 g, 7.61 mmol) The reaction mixture was stirred at 60° C. for 1 hr. Upon completion, reaction mixture was evaporated to dryness and added to ice water (20 mL). The pH was adjusted to pH10 using sat Na2CO3 solution (30 mL) and EtOAc (30 mL) was added. Saturated Rochelle's salt (20 mL) was added and the mixture stirred until separate layers were observed. The organic layer was separated and the aqueous layer extracted with EtOAc (2×5 mL). Combined organics were washed with saturated Rochelles salt (15 mL) followed by brine solution (15 mL) and dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound as a pale orange solid (500 mg, 68.7% yield); 1H NMR (250 MHz, DMSO) delta 8.11 (s, 1H), 7.75 (d, J=5.7 Hz, 1H), 7.37 (d, J=7.6 Hz, 1H), 6.67 (d, J=11.1 Hz, 1H), 6.08 (s, 2H), 5.75 (d, J=5.7 Hz, 1H), 5.37 (s, 2H); LC-MS: m/z+299.75 (M+H)+.

Provenance & Evidence