Water → HCID 68579653, compound

HRID 2046308Notes

Reaction equation

HRID 2046308 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[NH:10][C:11]([CH3:26])([C:13]1[NH:14][C:15](=[O:25])[CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][N:20]=2)[N:18]=1)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Li+].[CH3:30]OS(OC)(=O)=O.O>O1CCOCC1>[CH2:1]([O:8][C:9](=[O:27])[NH:10][C:11]([CH3:12])([C:13]1[N:14]([CH3:30])[C:15](=[O:25])[CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][N:20]=2)[N:18]=1)[CH3:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 62714Lithium hydrideHCID 136375850HCID 136375850, compound

Product 1

HCID 68579653HCID 68579653, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 0.13 g (0.36 mmol) of [1-Methyl-1-(6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yl)-ethyl]-carbamic acid benzyl ester in 1.5 mL of anhydrous dioxane was added 0.003 g (0.39 mmol) of lithium hydride. The resulting mixture was allowed to stir at 40° C. for 45 minutes. After cooling down to room temperature, 0.058 g (0.46 mmol) of dimethylsulfate was added and reaction mixture was heated at 60° C. for 12 h. After cooling to 0° C., water was added and the mixture extracted with ethyl acetate. The extracts were washed with a saturated aqueous solution of sodium chloride, dried and evaporated. The residue was purified on preparative thin layer chromatography eluting with a mixture of dichloromethane/methanol/aqueous ammonia solution (29%) in the proportions 95/5/0.5 to afford 0.015 g (11%) of the desired compound as a colorless oil.

Workup

  1. temperatureAfter cooling down to room temperature
  2. customreaction mixture
  3. temperaturewas heated at 60° C. for 12 h
  4. temperatureAfter cooling to 0° C.
  5. extractionthe mixture extracted with ethyl acetate
  6. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  7. customdried
  8. customevaporated
  9. customThe residue was purified on preparative thin layer chromatography
  10. washeluting with a mixture of dichloromethane/methanol/aqueous ammonia solution (29%) in the proportions 95/5/0.5

Sources & evidence

ORD record
ord-b810ea98c94348258466fcdc846eb3a8
Source dataset
uspto-grants-2013_11
Patent number
US08592436B2

Reaction notes

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