HCID 11493075, compound → 1-(2-Deoxypentofuranosyl)-4-hydroxy-5-pentylpyrimidin-2(1H)-one

HRID 1781572Notes

Reaction equation

HRID 1781572 reaction equation
[C:1]([C:6]1[C:7](=[O:21])[NH:8][C:9](=[O:20])[N:10]([CH:19]=1)[C@@H:11]1[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13]([OH:14])[CH2:12]1)#[C:2][CH2:3][CH2:4][CH3:5]>CO.[Pd]>[CH2:1]([C:6]1[C:7](=[O:21])[NH:8][C:9](=[O:20])[N:10]([CH:19]=1)[C@@H:11]1[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13]([OH:14])[CH2:12]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 1

HCID 11493075HCID 11493075, compound

Product 1

HCID 5127361-(2-Deoxypentofuranosyl)-4-hydroxy-5-pentylpyrimidin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1.03 g (3.50 mmol) of 5-(1-pentynyl)-2'-deoxyuridine in 25 mL of MeOH was added a catalytic amount of 10% Pd on charcoal. The mixture was hydrogenated under 300 psi of H2 for 14 h at room temperature. The mixture was filtered through Celite and concentrated, affording a quantitative yield of product.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-775c308cf3824ac2aaae6e5316af307d
Source dataset
uspto-grants-1997_05
Patent number
US05633360

Reaction notes

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