Ethyl 2-pyrimidineacetate

To a solution of diethylmalonate (6.65 mL, 43.65 mmol) in DMF (30 mL) at -78 °C, was added NaH (1.76 g, 52.38 mmol, 60percent dispersion in mineral oil). The reaction was stirredfor 10 min at -78 °C, warmed to room temperature and 2-chloropyrimidine (1.0 g, 8.73 mmol)in DMF (3 mL) was added. The reaction mixture was heated to 80 °C for 72 hours, then to120 °C for 18 hours, and upon completion was cooled to room temperature. The solution was15 quenched by addition of IN HCl, neutralized with saturated aqueous NaHC03 and extractedwith EtOAc (3X). The combined organics were dried over Na2S04, filtered, concentrated andpurified by flash chromatography on silica gel (0-1 00percent EtOAc in hexanes) to give the titlecompound as a yellow-orange oil (1.34 g, 92percent). MS 167 (MH+).To a solution of diethylmalonate (6.65 mL, 43.65 mmol) in DMF (30 mL) at -78 °C, was added NaH (1.76 g, 52.38 mmol, 60percent dispersion in mineral oil). The reaction was stirredfor 10 min at -78 °C, warmed to room temperature and 2-chloropyrimidine (1.0 g, 8.73 mmol)in DMF (3 mL) was added. The reaction mixture was heated to 80 °C for 72 hours, then to120 °C for 18 hours, and upon completion was cooled to room temperature. The solution was15 quenched by addition of IN HCl, neutralized with saturated aqueous NaHC03 and extractedwith EtOAc (3X). The combined organics were dried over Na2S04, filtered, concentrated andpurified by flash chromatography on silica gel (0-1 00percent EtOAc in hexanes) to give the titlecompound as a yellow-orange oil (1.34 g, 92percent). MS 167 (MH+).To a mixture of To a solution of To a solution of diethylmalonate (6.65 mL, 43.65 mmol) in DMF (30 mL) at -78 C, was added NaH (1.76 g, 52.38 mmol, 60% dispersion in mineral oil). The reaction was stirredfor 10 min at -78 C, warmed to room temperature and 2-chloropyrimidine (1.0 g, 8.73 mmol)in DMF (3 mL) was added. The reaction mixture was heated to 80 C for 72 hours, then to120 C for 18 hours, and upon completion was cooled to room temperature. The solution was15 quenched by addition of IN HCl, neutralized with saturated aqueous NaHC03 and extractedwith EtOAc (3X). The combined organics were dried over Na2S04, filtered, concentrated andpurified by flash chromatography on silica gel (0-1 00% EtOAc in hexanes) to give the titlecompound as a yellow-orange oil (1.34 g, 92%). MS 167 (MH+).

Molecular Weight:166.18
XLogP3:0.4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:166.074227566
Monoisotopic Mass:166.074227566
Topological Polar Surface Area:52.1
Heavy Atom Count:12
Complexity:144
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes