Hydrogen iodide → 4-iodo-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

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Reaction Steps

A mixture of 4-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (1020 mg, 2.65 mmol) and 67% hydriodic acid solution (0.499 mL, 6.63 mmol) in CH2Cl2 (10 mL) was stirred at room temperature for 19 h. The reaction mixture was diluted with NaHCO3 (30 mL) and extracted with EtOAc (2×40 mL). The organic extract was washed with saturated NaCl (20 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow solid. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 50% CH2Cl2/hexanes to give 4-iodo-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (826 mg, 1.734 mmol, 65.4% yield) as a mixture of product and starting material (3:1).

Provenance & Evidence