Sodium hydride → 3-(2-Furylmethyl)-7-methylxanthine

To a stirring suspension of 7-methylxanthine (2.54 g, 15.3 mmol) in dimethylsulfoxide (80 ml) was added sodium hydride (0.37 mg, 15.3 mmol) in one portion. After stirring for 30 minutes, freshly prepared furfuryl bromide (2.5 g, 15.3 mmol) was added neat. After stirring at room temperature for 18 hours, the reaction was quenched by addition of water (150 ml). Saturated aqueous sodium chloride solution (30 ml) was added and the mixture was extracted with chloroform (4×50 ml). The combined extracts were washed with saturated aqueous sodium bicarbonate solution (3×50 ml), with saturated aqueous sodium chloride solution (2×50 ml) and dried over a mixture of sodium sulfate and activated charcoal. After filtration through a pad of celite, the solvent was evaporated under reduced pressure. The residue was treated with ethyl acetate. The solid was filtered, rinsed with cold ethyl acetate (2×25 ml) and vacuum dried to give 3-(2-furylmethyl)-7-methylxanthine (0.54 g, 14% yield) as a beige solid.

1. stirringAfter stirring at room temperature for 18 hours
2. customthe reaction was quenched by addition of water (150 ml)
3. additionSaturated aqueous sodium chloride solution (30 ml) was added
4. extractionthe mixture was extracted with chloroform (4×50 ml)
5. washThe combined extracts were washed with saturated aqueous sodium bicarbonate solution (3×50 ml), with saturated aqueous sodium chloride solution (2×50 ml)
6. dry with materialdried over a mixture of sodium sulfate and activated charcoal
7. filtrationAfter filtration through a pad of celite
8. customthe solvent was evaporated under reduced pressure
9. additionThe residue was treated with ethyl acetate
10. filtrationThe solid was filtered
11. washrinsed with cold ethyl acetate (2×25 ml) and vacuum
12. customdried

ORD-Eintrag

ord-30022bd8bf3542c2a1c876095e283584

Quelldatensatz

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06774130B2