Formic Acid → HCID 178518756, compound

HRID 1641489Notes

Reaction equation

HRID 1641489 reaction equation
[F:1][C:2]1[C:3](=[O:22])[NH:4][C:5](=[O:21])[N:6]([C@H:8]2[CH2:11][C@@H:10]([CH2:12][O:13]CC3C=CC=CC=3)[CH2:9]2)[CH:7]=1.C(O)=O.[H][H]>[Pd].C(O)C>[F:1][C:2]1[C:3](=[O:22])[NH:4][C:5](=[O:21])[N:6]([C@H:8]2[CH2:9][C@@H:10]([CH2:12][OH:13])[CH2:11]2)[CH:7]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 178418361HCID 178418361, compoundHCID 178518757HCID 178518757, compound

Product 1

HCID 178518756HCID 178518756, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-fluoro-1-[cis-3-(benzyloxymethyl)cyclobutyl]uracil (250 mg, 0.79 mmol), 10% palladium on activated carbon (50 mg) and formic acid (2 mL) in ethanol (20 mL) was placed under 45 PSI of hydrogen on a Parr Apparatus for 2 h. The mixture was filtered through a pad of Celite and the charcoal was washed with ethanol (3×20 mL). Combined filtrates were concentrated under vacuum and purified by a short column of silica gel with 4% MeOH in CH2Cl2 to give 5-fluoro-1-[cis-3-(hydroxymethyl)cyclobutyl]uracil (159 mg, 94%) as a white solid.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washthe charcoal was washed with ethanol (3×20 mL)
  3. concentrationCombined filtrates were concentrated under vacuum
  4. custompurified by a short column of silica gel with 4% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-06a311ebdd71423381d6c2e9c37bbb6b
Source dataset
uspto-grants-2012_02
Patent number
US08114994B2

Reaction notes

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