Potassium Carbonate → 2-(4-(((Benzyloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

In a three-necked round bottom flask equipped with a mechanical stirrer and a nitrogen inlet was placed methyl bromacetate (7.82 mL, 82.6 mmol) and a suspension of N4 -benzyloxycarbonyl-cytosine (9, 21 g, 82.6 mmol) and potassium carbonate (11.4 g, 82.6 mmol) in dry DMF (900 mL). The mixture was stirred vigorously overnight, filtered, and evaporated to dryness, in vacuo. Water (300 mL) and 4N hydrochloric acid (10 mL) were added, the mixture was stirred for 15 minutes at 0° C., filtered, and washed with water (2×75 mL). The isolated precipitate was treated with water (120 mL), 2N sodium hydroxide (60 mL), stirred for 30 minutes, filtered, cooled to 0° C., and 4N hydrochloric acid (35 mL) was added. The title compound was isolated by filtration, washed with water, recrystallized from methanol (1000 mL) and washed with ether. This afforded 7.70 g (31%) of pure title compound. The mother liquor from recrystallization was reduced to a volume of 200 mL and cooled to 0° C. This afforded an additional 2.30 g of a material that was pure by tlc but had a reddish color. M.p. 266°-274° C. Anal. for C14H13N3O5. Found(calc.); C: 55.41(55.45); H: 4.23(4.32); N: 14.04(13.86). 1H-NMR (90 MHz; DMSO-d6): 8.02 ppm (d,J=7.32Hz, 1H, H-6); 7.39 (s, 5H, Ph); 7.01 (d, J=7.32Hz, 1H, H-5); 5.19 (s, 2H, PhCH2 --); 4.52 (s, 2H).

Provenance & Evidence