Sodium hydride → 3-Methyl-1,7-bis(3',4'-dihydroxybenzyl)xanthine

Temperatur

60 °C

A solution of 3-methyl xanthine (200 mg, 1.2 mmol) in N,N-dimethylformamide (5 ml) was treated with 3,4-bis-benzyloxy-benzyl chloride (Lot #PRO-04-36B, 1.02 g, 3 mmol) and NaH (96 mg, 4 mmol) and 0.5 equivalent tetrabutyl ammonium iodide and was heated to 60° C. for 12 hrs. The reaction mixture was poured in water and extracted with ethyl acetate (3×30 ml). The combined organic extract was washed with water, brine solution (30 ml) each and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the product was purified by flash column chromatography over silica gel using 40% ethyl acetate/hexane to yield the desired product, 600 mg, 78% yield. This product was dissolved in ethyl acetate (25 ml) and methanol (10 ml) and acetic acid (1 ml) and hydrogenated in presence of 10% Pd—C at 55 PSI for 2 hr. Catalyst was filtered off and the solvent was removed under reduced pressure. The residue was purified on a silica gel column eluting with 50% ethyl acetate in hexane to 100% ethyl acetate. The desired product was isolated as an off white solid, Yield=400 mg PD 151.

1. extractionextracted with ethyl acetate (3×30 ml)
2. extractionThe combined organic extract
3. washwas washed with water, brine solution (30 ml) each and
4. dry with materialdried over anhydrous magnesium sulfate
5. customThe solvent was removed under reduced pressure
6. customthe product was purified by flash column chromatography over silica gel using 40% ethyl acetate/hexane

ORD-Eintrag

ord-8c8b592e3b714cb9a35323b83574cd2d

Quelldatensatz

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09169255B2