Water → HCID 57191409, compound

Participants

Reaction Conditions

Reaction Steps

(±)-7-Amino-3-(2-cyclopenten-1-yl)-1,2,3-triazolo[4,5-d]pyrimidine (4.80 g, 23.7 mmol), N-methylmorpholine N-oxide monohydrate (3.15 g, 26.1 mmol as 97%), water (35 ml), t-butylalcohol (175 ml) and 2.5% osmium tetroxide in t-butyl alcohol (1.0 ml) were refluxed for 3 hours and then stirred at 25° C. for 18 hours. The resulting mixture was evaporated to dryness and chromatographed on silica gel. Title compound was eluted with MeOH:CHCl3 /1:3 to give white crystals after two recrystallizations from ethanol-water (3.74 g, 67%); mp 244°-245° C.; 1H-NMR (Me2SO-d6) δ8.26 (s, 1, H-5'), 8.35 and 8.05 (both br s) overlapping 8.26 (s) (total 3 protons, tautomers NH2 and H-5'), 5.2-5.0 (m) overlapping 5.01 (d, J=7.3) (total 2, OH and H-3 ), 4.72 (d, J=3.5, 1, OH), 4.5-4.4 (m, 1, H-2), 4.1-4.0 (m, 1, H-1), 2.4-1.6 (m, 4, two CH2).

Provenance & Evidence