Uracil → 1,3-Dimethyl-5-formyluracil

HRID 642855Notes

Reaction equation

HRID 642855 reaction equation
[CH:1]([C:3]1[C:4](=[O:10])[NH:5][C:6](=O)NC=1)=[O:2].[H-].[Na+].CI.N1C=CC(=O)NC1=O.[CH3:23][N:24]([CH:26]=[O:27])[CH3:25]>O.CO>[CH3:23][N:24]1[CH:25]=[C:3]([CH:1]=[O:2])[C:4](=[O:10])[N:5]([CH3:6])[C:26]1=[O:27]

Participants

8

Reactant 5

HCID 1174UracilHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3045905-Formyluracil

Product 1

HCID 4530921,3-Dimethyl-5-formyluracilYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a slurry of 400mg of 5-formyluracil (2.8 mM) in DMF (10 mL) at room temperature was added sodium hydride (280 mg, 7 mM, 60% in oil). After stirring for 30 min., MeI (1.013 g, 7.2 mM) was added. When the turbid reaction mixture became a homogeneous yellow solution tlc revealed the absence of starting uracil. The reaction mixture was treated with MeOH and water, concentrated on the rotovap and the residue partitioned between MeOH and hexane. The MeOH fraction was concentrated and the residue partitioned between chloroform and water. The organic phase dried (MgSO4), filtered and concentrated to give 420 mg (89% yield) of 1,3-dimethyl-5-formyluracil as an off-white waxy solid. 1H-NMR (DMSO-d6), δ=9.82 (s, 1H), 8.52 (s, 1H), 3.43 (s, 3H), 3.2 (s, 3H). LC/MS; rt=0.34 mins. m/z=169, [M+H]+.

Workup

  1. customWhen the turbid reaction mixture
  2. concentrationconcentrated on the rotovap
  3. customthe residue partitioned between MeOH and hexane
  4. concentrationThe MeOH fraction was concentrated
  5. customthe residue partitioned between chloroform and water
  6. dry with materialThe organic phase dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-76088762265749b788fd0b14f23afda4
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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