Sodium Carbonate → 1-Methyl-7-(pivaloyloxymethyl)xanthine

Participants

Reaction Steps

To a mixture of 1-methylxanthine (844 mg, 5.08 m moles) and sodium carbonate (538 mg, 5.08 m moles) in 20 ml of dry DMF under nitrogen was slowly added over a period of 1 hour a solution of chloromethylpivalate (828 μl, 5.59 m mole) in 6 ml DMF at room temperature and the reaction mixture stirred overnight. The mixture was filtered, the filtrate evaporated to dryness and the residue triturated with 50 ml of 10 vol. %. EtOH/CHCl3. The solids obtained were starting material and the organic phase was chromatographed (10 vol. % EtOH/CHCl3) on silica gel plates. Two products were observed by eluting with 125 ml of 10 vol. % EtOH/CHCl3 and the band Rf, 0.48 obtained as 365 mg of the desired product. The other band proved to be the 3,7 -disubstituted material.

Provenance & Evidence