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

HRID 65196Notes

Reaction equation

HRID 65196 reaction equation
[CH2:1]([C:8]1[C:9](=[O:36])[NH:10][C:11](=[O:35])[N:12]([CH2:14][O:15][CH:16]([CH2:26][O:27]CC2C=CC=CC=2)[CH2:17][O:18]CC2C=CC=CC=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.Cl.[Pd]>[CH2:1]([C:8]1[C:9](=[O:36])[NH:10][C:11](=[O:35])[N:12]([CH2:14][O:15][CH:16]([CH2:17][OH:18])[CH2:26][OH:27])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 543595235-Benzyl-1-[(1,3-bis(benzyloxy)-2-propoxy)methyl]uracil

Product 1

HCID 1259141-((2-Hydroxy-1-(hydroxymethyl)ethoxy)methyl)-5-benzyluracilYield 87%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

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).

Workup

  1. customAfter the theoretical amount of hydrogen had been absorbed
  2. filtrationthe solution was filtered
  3. customevaporated to dryness
  4. washeluted with methylene chloride-methanol (12:1)

Sources & evidence

ORD record
ord-2a12036676dd404f9a465f8f1c00f8d9
Source dataset
uspto-grants-1986_09
Patent number
US04613604

Reaction notes

Loading…