Propargyl bromide → HCID 86755938, compound

Participants

Reaction Steps

Propargyl bromide (11.8 ml, 105.9 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (20.62 ml, 135.2 mmol) were added to a suspension of inosine (27.56 g, 102.8 mmol) in dimethylacetamide (590 ml). The reaction mixture was stirred at room temperature overnight under argon, at which time TLC in chloroform/methanol (85:15) demonstrated disappearance of starting material. The reaction was terminated by addition to the suspension 3.5 L of ether/hexane (1:1) with storage at about -20 degrees C. overnight. While still chilled, solvent was decanted from the resulting gum, which was then dissolved in methanol and evaporated in vacuo (oil pump) onto silica gel. The product was isolated by silica gel chromatography using chloroform/methanol (95:5). The product was then characterized using mass spectrometry and proton NMR data. The mass spectrometer gave the following results: FABMS(glycerol), m/z 307 (MH+). The NMR data gave the following results: 1H-NMR (DMSO-d6): 8.50 (1H, s, H2); 8.39 (1H, s, H8); 5.87, 5.84 (1H, d, H1'); 5.51, 5.49 (1H, d, 2--OH); 5.23, 5.20 (1H, d, 3'--OH); 5.05 (1H, t, 5'--OH); 4.84, 4.83 (2H, d, CH2); 4.44 (1H, m, H2); 4.11, (1H, m, H3'), 3.92 (1H, m, H4'); 3.62 (1H, m, H5'); 3.57 (1H, m, H5'); 3.41 (1H, t, CH). Characterization with mass spec. and NMR yielded data consistent with the structure of 1-propargylinosine.

Provenance & Evidence