Oxalyl chloride → HCID 73775704, compound

Participants

Reaction Steps

(100 mg, 0.39 mmol) 5-(3-Chloro-phenylethynyl)-pyrimidine-2-carboxylic acid (Example 4, step 1) was suspended in dichloromethane (1 ml) and DMF (10 μl). Oxalyl chloride (51 μl, 0.59 mmol, 1.5 equiv.) was added drop wise at room temperature and the mixture was stirred for 1 hour at reflux. The reaction mixture was then added to a mixture of diisopropylethylamine (235 μl, 1.34 mmol, 3.3 equiv.) and 3,3-dimethylmorpholine (46 mg, 0.40 mmol, 1 equiv.) in THF (2 ml). The mixture was stirred for 16 hours at room temperature and evaporated in presence of Isolute® sorbent to dryness. The crude product was purified by flash chromatography with a 20 g silica gel column eluting with heptane:ethyl acetate 100:0→0:100. The desired (3,3-dimethyl-morpholin-4-yl)[5-(3-chloro-phenylethynyl)-pyrimidin-2-yl]-methanone (120 mg, 94% yield) was obtained as a white solid, MS: m/e=356.6/358.6 (M+H+).

Provenance & Evidence