Sodium → 5-Ethynyluridine

HRID 566945Notes

Reaction equation

HRID 566945 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[CH:26]=[C:25]([C:27]#[C:28][Si](C)(C)C)[C:23](=[O:24])[NH:22][C:20]1=[O:21])(=O)C.[Na]>CO>[C:27]([C:25]1[C:23](=[O:24])[NH:22][C:20](=[O:21])[N:19]([CH:26]=1)[C@@H:6]1[O:7][C@H:8]([CH2:14][OH:15])[C@@H:9]([OH:10])[C@H:5]1[OH:4])#[CH:28]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 106718922',3',5'-Tri-O-Acetyl-5-[2-(trimethylsilyl)ethvnyl]uridine

Product 1

HCID 148859605-Ethynyluridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The product of stage b) (9.5 g, 24 mmol) was dissolved in methanol (200 mL) and diluted with a solution containing sodium (0.8 g) and methanol (100 mL). The reaction was stirred at room temperature for 2 hours and was then neutralized using Dowex 50W-X8 (H+form) resin. The resin was removed by filtering and washed with methanol. The filtrate was concentrated in vacuo to give 4.85 g of a beige solid. The compound was purified on a Waters Prep 500 reverse phase C column which was eluted with H2O/MeOH 85:15 (v:v) to give 1.2 g of the title product (white solid). Impure fractions were re-chromatographed. An additional 1.94 g of product were obtained.

Workup

  1. additiondiluted with a solution
  2. customThe resin was removed
  3. filtrationby filtering
  4. washwashed with methanol
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a4b24c95579d4f3d9631508f8be33b8e
Source dataset
uspto-grants-2001_01
Patent number
US06177436B1

Reaction notes

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