Hydrochloric Acid → 6-Chloro-2-imino-N-methyl-N-phenyl-1,2-dihydropyrimidin-4-amine

Participants

Reaction Steps

A 20-mL screw-cap vial was charged with N-methylaniline (0.653 g, 6.1 mmol), 4,6-dichloro-2-pyrimidinamine (1 g, 6.1 mmol), 1,4-dioxane (5 mL), and HCl (0.152 mL, 0.61 mmol, 4M in 1,4-dioxane). The vial was capped and stirred at reflux overnight. At this time, LCMS analysis indicated good conversion to the desired product, so the reaction mixture was poured into 1:1 NaHCO3 (sat) and water (20 mL) and extracted with EtOAc (3×50 mL). The combined organics were dried (Na2SO4) and concentrated. The solid residue was triturated with CH2Cl2, to yield the title compound (644 mg) as an off-white solid. LC-MS (ES) m/z=235 [M+H]+.

Provenance & Evidence