2,2-Dimethoxypropane → 5-fluoro-1-[(4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrimidine-2,4-dione

HRID 728614

Reaction equation

HRID 728614 reaction equation
[F:1][C:2]1[C:3](=[O:18])[NH:4][C:5](=[O:17])[N:6]([CH:16]=1)[C@@H:7]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1[OH:9].CO[C:21](OC)([CH3:23])[CH3:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CC(C)=O>[CH3:22][C:21]1([CH3:23])[O:9][CH:8]2[CH:10]([C@@H:12]([CH2:13][OH:14])[O:15][C@H:7]2[N:6]2[C:5](=[O:17])[NH:4][C:3](=[O:18])[C:2]([F:1])=[CH:16]2)[O:11]1

Participants

6

Reactant 4

HCID 64952,2-DimethoxypropaneHCID 94275-FluorouridineHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 2008315-fluoro-1-[(4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrimidine-2,4-dioneYield 84%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 750 ml of acetone were added 15 g of 5-fluorouridine, 7.5 ml of 2,2-dimethoxypropane and 1.1 g of p-toluenesulfonic acid monohydrate, and the mixture was reacted at room temperature for 4.5 hours under stirring. After allowed to stand overnight at room temperature, 5 g of sodium hydrogen carbonate was added to the reaction mixture and the mixture was stirred at room temperature for 2.5 hours. After insolubles were filtered off, the filtrate was condensed under reduced pressure, and the obtained crystals were recrystallized from ethanol to give 15.7 g (Yield: 84%) of the title compound as colorless needle crystals.

Workup

  1. customthe mixture was reacted at room temperature for 4.5 hours
  2. stirringthe mixture was stirred at room temperature for 2.5 hours
  3. filtrationAfter insolubles were filtered off
  4. customcondensed under reduced pressure
  5. customthe obtained crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-b2094df13ded4c48ba4c120b1194933f
Source dataset
uspto-grants-1991_09
Patent number
US05049551

Linked notes

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