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

Participants

Reaction Conditions

Reaction Steps

In a three necked round bottomed flask equipped with mechanical stirring and nitrogen coverage was placed methyl bromacetate (7.82 ml; 82.6 mmol) and a suspension of N4-benzyloxycarbonyl-cytosine (9, 21.0 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 4 N 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 min, filtered, cooled to 0° C., and 4 N hydrochloric acid (35 ml) was added. The title compound was isolated by filtration, washed thoroughly with water, recrystallized from methanol (1000 ml) and washed thoroughly with ether. This afforded 7.70 g (31%) of pure compound. The mother liquor from the 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 colour. 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=7.32 Hz, 1H, H-6); 7.39(s, 5H, Ph); 7.01(d, J=7.32 Hz, 1H, H-5); 5.19 (s, 2H, PhCH2—); 4.52 (s, 2H).

Provenance & Evidence