Dimethylformamide → Benzoyl cytosin-1-ylacetate

Participants

Reaction Conditions

Reaction Steps

Reference is made to FIG. 1 where to cytosine (20 g, 0.18 mmol) in 400 mL DMF was added 7.2 g (0.18 mmol) of NaH (disp. in oil 60%). The mixture was heated to 50° C. and stirred for 2 h under nitrogen. After cooling to room temperature, 29 mL (1.1 eq.) of benzyl bromoacetate was added over 2 h. After stirring overnight, the dark suspension was filtered and the filtrate washed with cold DMF and 0.2 M sodium bicarbonate. The product (1) was crystallized from ethanol. Yield: 37 g (79%). 1H NMR (d6-DMSO): δ 4.56 (s, 2 CH2O), 5.24 (s, 2 H, CH2CO), 5.77 (d, 1 H, H5), 7.20 (dd, 2 H, NH2), 7.45 (m, 5 H, aromatic), 7.65 (d, 1 H, H6). MS (FAB) m/z 260 (M+H)+ (calcd 260).

Provenance & Evidence