Methane → 7-(2,3-Dihydroxypropyl)-1,3-di-n-propylxanthine

Participants

Reaction Steps

A suspension of 1,3-di-n-propylxanthine (250.1 g., 1.06 mole) in water (300 ml.) was treated with sodium hydroxide solution (50%, 85 ml.). The mixture was filtered, and evaporated to dryness. The residue obtained was treated with a solution of 1-chloro-2,3-dihydroxypropane (170 g., 1.59 mole) in isopropanol (700 ml.). The mixture was stirred at reflux overnight, filtered, and evaporated to dryness to obtain a brown gummy residue. This residue was dissolved in isopropyl alcohol, and stirred overnight with charcoal (20 gm.). The mixture was filtered, concentrated and allowed to crystallize over night at 0° to -5° C. The crystals were filtered, suspended in ether, refiltered and air dried to yield white crystals (224 g., 72.17%), melting point 88° - 91°. Tlc (5μl of a 5% solution) on a silica plate developed in chloroform:methanol (9.5:0.5) showed one spot. IR and NMR spectra were consistent with the proposed structure.

Provenance & Evidence