(2R,3R)-1-Benzyloxy-3-(tert-butyldimethylsiloxy)-2-((2-oxo-4-(1H-1,2,4-triazol-1-yl)pyrimidin-1(2H)-yl)methyl)butane → (2R,3R)-1-Benzyloxy-3-(tert-butyldimethylsiloxy)-2-((4-amino-2-oxo-pyrimidin-1(2H)-yl)methyl)butane

Participants

Reaction Steps

A solution of 18 (1.5 g, 3.2 mmol) in 100 ml of 6 M NH3/MeOH was heated at 100° C. in a Parr bomb for 2 days. The reaction was cooled, concentrated and chromatographed on silica eluting with 10% MeOH in ethyl acetate. Concentration of the product-containing fractions afforded 1.27 g (95%) of 19 as an off-white amorphous solid. 1H NMR (DMSO-d6): δ 7.43 (d, J=7.2 Hz, 1H), 7.29 (m, 5H), 6.97 (br s, 2H), 5.58 (d, J=7.2 Hz), 4.39 (d, J=1.8 Hz, 2H), 3.98 (m, 1H), 3.83 (m, 1H), 3.51 (m, 1H), 3.35 (m, 2H), 2.06 (m, 1H), 1.14 (d, J=6.3 Hz, 3H), 0.85 (s, 9H), 0.02 (s, 3H), 0.00 (s, 3H).

Provenance & Evidence