Hydrochloric Acid → HCID 68690649, compound

Participants

Reaction Steps

nButyllithium (1.50 mL of a 2.82 M solution in hexanes, 4.23 mmol) was added dropwise over 10 minutes to a solution of diisopropylamine (370 mg, 3.66 mmol) and anhydrous THF (10 mL) at 0° C. under an atmosphere of N2. The mixture was stirred for 10 minutes then cannulated into a −45° C. solution of (2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl)-N-(diphenylmethylene)methanamine (1.00 g, 2.83 mmol) and anhydrous THF (10 mL) under a N2 atmosphere. The reaction mixture was stirred for 30 minutes then ethyl acrylate (341 mg, 3.41 mmol) was added dropwise over 10 minutes. The reaction mixture was warmed to rt then stirred for 12 h. The mixture was cooled to 0° C. then HCl (50 ml, 10% v/v aqueous) was added dropwise over 15 minutes. The solution was warmed to rt, extracted with ethyl ether (3×30 mL), and the aqueous layer was adjusted to pH=8.5 with solid K2CO3. The resulting solution was extracted with DCM (3×30 mL), combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum to afford 1.10 g of amino-4-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-butyric acid ethyl ester as a brown solid.

Provenance & Evidence