Stannous chloride dihydrate → 4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-N-(5-bromo-2-nitrophenyl)pyrimidine-2,4-diamine (5.06 g, 16.32 mmol) in ethanol (110 mL) was added tin(II) chloride dihydrate (12.89 g, 57.11 mmol). The reaction mixture was stirred at 65° C. for 2 hr. The reaction mixture was evaporated to dryness and ice-water added. The pH of the mixture was adjusted to 10 using saturated aqueous Na2CO3 solution. EtOAc was added followed by saturated aqueous Rochelles salt (potassium sodium tartrate). The resulting mixture was stirred until separate layers were observed. The organic layer was extracted and the extraction repeated (2×) with EtOAc and DCM. Combined organic layer were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound as a pale yellow solid: 1H NMR (250 MHz, DMSO) δ 5.05 (2H, br. s), 5.79 (1H, d, J=5.79 Hz), 6.08 (2H, br. s), 6.68 (1H, d, J=8.53 Hz), 7.02 (1H, dd, J=8.60, 2.36 Hz), 7.36 (1H, d, J=2.28 Hz), 7.75 (1H, d, J=5.63 Hz), 8.15 (1H, s); LC-MS: m/z=+279.9, 281.9 (M+H)+.

Provenance & Evidence