Ethyl Bromide → Uridine, 2′-deoxy-5-ethoxy-

HRID 1439840Notes

Reaction equation

HRID 1439840 reaction equation
[OH:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1.[OH-].[Na+].[CH2:20](Br)[CH3:21]>CO.O>[CH2:20]([O:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1)[CH3:21]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 14798Sodium HydroxideHCID 966225168-36-5

Product 1

HCID 9795471Uridine, 2′-deoxy-5-ethoxy-Yield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The 2'-deoxy-5-hydroxyuridine (244 mg.,1mmol) was suspended in a mixture of methanol (10ml) and water (5ml) at room temperature, and 1 ml of 1.0N sodium hydroxide solution (1mmol) was added to generate the monoanion. Ethyl bromide (0.312ml, 4mmol) was added, and the reaction mixture was stirred for 16 hours. The solvent was removed in vacuo, and ethanol was added to and evaporated from the residue. The desired 5-ethoxy product was separated from small amounts of the 3 ethyl-5-ethoxy dialkyl byproduct by chromatography on a silica gel column using chloroform-methanol (9:1, v/v) as the solvent. Following crystallization from absolute ethanol, 5-ethoxy-2'-deoxyuridine was obtained in 52% yield (140 mg); mp 179°-181° C.; 1H NMR (methyl sulfoxide-d6),δ11.38 (1H, br s, NH), 7.58 (1H, s, H-6), 6.18 (1H, t, H-1'), 5.19 (1H, d, 3'-OH), 5.09 (1H, t, 5'-OH), 4.25 (1H, m, H-3'), 3.79 (3H, m. H4'and OCH2CH3 ), 3.59 (2H, br s,H-5'and H-5"), 2.10 (2H, m, H-2'and H-2") and 1.23ppm (3H, t, OCH2CH3). Anal. Calcd. for C11H16N2O6C, 48.53; H, 5.92; N, 10.29. Found: C, 48.69; H, 6.0-1; N, 10.36.

Workup

  1. customThe solvent was removed in vacuo, and ethanol
  2. additionwas added to and
  3. customevaporated from the residue
  4. customThe desired 5-ethoxy product was separated from small amounts of the 3 ethyl-5-ethoxy dialkyl byproduct by chromatography on a silica gel column
  5. customcrystallization from absolute ethanol

Sources & evidence

ORD record
ord-e1d3794edc0b4e72847ba373f9c951f4
Source dataset
uspto-grants-1996_03
Patent number
US05496810

Reaction notes

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