Hexamethyldisilazane → HCID 67675541, compound

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Reaction Steps

To 20 mL of hexamethyldisilazane (HMDS) is added 2.98 g (0.02 mole) of 4-amino-pteridine-2-one (30). The mixture is heated for 24 hours under reflux, with moisture excluded, to obtain a clear solution. The excess HMDS is removed under high vacuum to give 1-trimethylsilylamino-2-trimethylsilyloxy-pteridine as a viscous oil. The residue is dissolved in 200 mL of benzene and then 9.37 g (0.022 mole) of 2-deoxy-3,5- di-O-toluoyl-α-D-ribofuranosyl chloride, 4 g HgO, and 4 g HgBr2 are added and the mixture is refluxed for 5 hours. After cooling, the precipitate is filtered off, the flitrate evaporated to dryness and the residue dissolved in 100 mL of CHCl3. The solution is extracted twice with 100 mL of 20% KI. The organic layer is then dried over Na2SO4, again evaporated and the residue dissolved in a little ethyl acetate for silica-gel column chromatography with ethyl acetate/acetone 7:3. The first fraction contains excess sugar, the second fraction the α-anomer and last eluting fraction the β-deoxyriboside. Evaporation and recrystallization of the residue from ethanol gives 31.

Provenance & Evidence