Sodium Iodide → 4-N-(2-amino-5-iodophenyl)pyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

A pressure tube containing copper(I) iodide (61.2 mg, 0.32 mmol), sodium iodide (963.18 mg, 6.43 mmol) and 4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine (900 mg, 3.21 mmol) was flushed with nitrogen before the addition of 1,4-dioxane (4.0 mL), DMF (4.0 ml) and N,N′-dimethylethane-1,2-diamine (0.035 ml, 0.32 mmol). The vessel was sealed and stirred at 115° C. overnight. After cooling to RT, the reaction mixture was poured into ice water (7 ml) and the resulting solution extracted with DCM (2×100 mL). The combined organics were dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (Biotage, 3-14% methanol gradient in DCM) furnished the title compound (600 mg, 57% yield); 1H NMR (500 MHz, DMSO) delta 5.04 (2H, d, J=11.6 Hz), 5.78-5.73 (1H, m), 6.11-6.02 (2H, m), 6.57 (1H, d, J=8.4 Hz), 7.18 (1H, dd, J=8.4, 2.0 Hz), 7.47-7.38 (1H, m), 7.75 (1H, d, J=5.3 Hz), 8.20-8.12 (1H, m); LC-MS: m/z=+327.8 (M+H)+.

Provenance & Evidence