Carbon Tetrachloride → 1-[(2-Chloroethoxy)methyl]-5-methyl-2,4(1H,3H)-pyrimidinedione

Participants

Reaction Steps

150 mg (0.75 mmol) 1-[(2-hydroxyethoxy)methyl]-5-methyl-2,4(1H,3H)-pyrimidinedione were dissolved in 10 ml pyridine and 1 g PS-triphenylphosphine resin (3 mmol/g) and 147 μl carbontetrachloride were added. The reaction was stirred at room temperature for 3 days. The reaction mixture was diluted with a mixture of ethyl acetate and methanol and centrifuged. The supernatant was decanted and the solvent was evaporated under reduced pressure. The residue, dissolved in ethyl acetate and a small amount of methanol, was purified by flash chromatography on silica gel (ethyl acetate). The fractions containing the product were pooled and the volume was reduced to about 3 ml. Upon addition of hexane the product crystallized to give 97 mg of white crystals. MS (ISP): 217.1 (M−H+). 1H-NMR (DMSO-d6): 1.77 (d, 3H), 3.69–3.77 (m, 4H), 5.10 (s, 2H), 7.59 (d, 1H), 11,32 (s, br, 1H).

Provenance & Evidence