Hydrochloric Acid → HCID 51353726, compound

Participants

Reaction Steps

A mixture of [(2S,5R)-5-methyl-2-morpholinyl]methanol (11.50 g, 65.2 mmol), 4,6-dichloro-N-methyl-2-pyrimidinamine (11.38 g, 63.9 mmol), and K2CO3 (19.87 g, 144 mmol) in EtOH (250 mL) was stirred at reflux under nitrogen for 23 hours. The mixture was cooled, poured into water (500 mL), and extracted with CH2Cl2 (3×400 mL). The extracts were dried (Na2SO4), filtered, and concentrated in vacuo to give a cream solid. The residue was purified by flash chromatography (400 g SiO2, 10-60% EtOAc in hexanes gradient). The product was collected and concentrated in vacuo to give a very sticky foam. The residue was taken up in Et2O (250 mL) and HCl (4.0 M in 1,4-dioxane, 10 mL) was added dropwise while the mixture was swirled. The solid that formed was collected by vacuum filtration and dried in the vacuum oven overnight to give a hydrochloride salt of the title compound (9.75 g) as a white solid. LC-MS (ES) m/z=273, 275 [M+H]+.

Provenance & Evidence