5-Benzyl-1-[(1,3-bis(benzyloxy)-2-propoxy)methyl]uracil → 1-((2-Hydroxy-1-(hydroxymethyl)ethoxy)methyl)-5-benzyluracil

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Reaction Steps

2 g (4.6 mmol) of 3a prepared as above was dissolved in 100 ml of glacial acetic acid and 0.2 ml of concentrated HCl. 5% Palladium on charcoal (1 g) was then added and the reaction mixture hydrogenated under 50 lbs pressure. After the theoretical amount of hydrogen had been absorbed, the solution was filtered and evaporated to dryness. The residue was placed on a silica gel column and eluted with methylene chloride-methanol (12:1) to give 1.1 g of 4a (87%). It was isolated as an oil and dried under vacuum over P2O5 for several days. UV (pH 1): λ max 266 nm (9400); pH 11: λ max 266 nm (6400). NMR(DMSO-d6): δ3.47 (s, 4H, CH2OH), 3.52 (s, 3H, CH2 at C5 and tert. H), 4.66 (t, 2H, OH) 5.20 (s, 2H, CH2 at N1), 7.24 (s, 5H, ArH), 7.65(s, 1H, C6 -H), 11.33 (s, 1H, NH).

Provenance & Evidence