Hexamethyldisilazane → HCID 22223251, compound

HRID 1744763

Reaction equation

HRID 1744763 reaction equation
[CH3:1][C:2]1[C:3](=[O:10])[NH:4][C:5](=[O:9])[NH:6][C:7]=1[CH3:8].[CH3:11][Si](C)(C)N[Si](C)(C)C>CN(C=O)C>[CH3:11][N:6]1[C:7]([CH3:8])=[C:2]([CH3:1])[C:3](=[O:10])[NH:4][C:5]1=[O:9]

Participants

4

Reactant 2

HCID 13838HexamethyldisilazaneHCID 960315,6-Dimethyluracil

Product 1

HCID 22223251HCID 22223251, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

6.00 g (42.9 mmol) 5,6-dimethyluracil was dissolved in 26 mL of hexamethyldisilazane and 2.1 mL DMF. The mixture was heated for 11 hours at 150° C. and the excess of hexamethyldisilazane was removed under reduced pressure. Toluene was added to the mixture and evaporated off under reduced pressure to remove any residual hexamethyldisilazane. The residue was dissolved in 25 mL of iodomethane, refluxed for 2 hours, the excess iodomethane then evaporated off under reduced pressure and the residue recrystallized from deionised water yielding after drying 5.76 g (87%) of 1,5,6-trimethyluracil (m.p. 254–257° C., lit. 256–258° C.).

Workup

  1. customthe excess of hexamethyldisilazane was removed under reduced pressure
  2. additionToluene was added to the mixture
  3. customevaporated off under reduced pressure
  4. customto remove any residual hexamethyldisilazane
  5. dissolutionThe residue was dissolved in 25 mL of iodomethane
  6. temperaturerefluxed for 2 hours
  7. customthe excess iodomethane then evaporated off under reduced pressure
  8. customthe residue recrystallized from deionised water yielding
  9. dry with materialafter drying 5.76 g (87%) of 1,5,6-trimethyluracil (m.p. 254–257° C., lit. 256–258° C.)

Sources & evidence

ORD record
ord-aaa8c976615b4462a9470aef40471c31
Source dataset
uspto-grants-2006_03
Patent number
US07018786B2

Linked notes

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