Ammonium Chloride → HCID 69809502, compound

Participants

Reaction Steps

To a solution of 4-(4-fluoro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester (205 mg, 0.78 mmol) in THF (3 mL) was added lithium hexamethyldisilazide (LiHMDS, 0.78 mL of 1M THF solution, 0.78 mmol) at 0° C. under argon atmosphere. The reaction mixture was stirred for 10 minutes, and then 2-trimethylsilylethyoxymethyl chloride (SEMCl, 0.137 mL, 0.78 mmol) was added dropwise at 0° C. The mixture was allowed to reach rt and was stirred overnight. Saturated aqueous NH4Cl was added and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried under Na2SO4, filtered and concentrated to dryness under reduced pressure. Purification of the residue by flash column (hexane/ethyl acetate gradient) gave 4-(4-fluoro-phenyl)-2-oxo-1-propoxymethyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester (155 mg, 51%).

Provenance & Evidence