3-(Chloromethyl)pyridine → HCID 131721043, compound

Participants

Reaction Steps

The procedure described in Example 140B was followed with a solution of 3-N-adamantan-1-yl-3-oxo-2-pyrimidin4-ylmethyl-propanoic acid, ethyl ester [prepared as described in Example 144] (0.225 g, 0.629 mmol) in EtOH (3 mL), a 21% by weight solution of NaOEt in EtOH (0.306 mL, 0.818 mmol), and a solution of 3-chloromethylpyridine (0.088 g, 0.692 mmol) in EtOH (1 mL) except that the reaction was heated at 60° C. overnight (16 hours). After flash chromatography (75 to 100% EtOAc-hexane), the title compound, free base (0.119 g, 42%) was obtained as a yellow solid. A portion of the free base (0.039 g, 0.087 mmol) was treated with ethanolic HCl as described in Example 140C to give the dihydrochloride salt (0.030 g, 66%) as a light yellow solid.

Provenance & Evidence