Carbon Dioxide → HCID 20026139, compound

HRID 1380829Notes

Reaction equation

HRID 1380829 reaction equation
[Cl:1][CH2:2][C:3]1[NH:8][C:7](=O)[NH:6]C(=O)C=1.F[B-](F)(F)F.C([O+:18]([CH2:21][CH3:22])[CH2:19][CH3:20])C.[C:23](=[O:26])([O-])[O-].[K+].[K+].[C:29](=O)=O>ClC(Cl)CCl>[Cl:1][CH2:2][C:3]1[CH:22]=[C:21]([O:18][CH2:19][CH3:20])[N:6]=[C:7]([O:26][CH2:23][CH3:29])[N:8]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 732736-(Chloromethyl)-2,4(1H,3H)-pyrimidinedioneHCID 2723982Triethyloxonium tetrafluoroborate

Product 1

HCID 20026139HCID 20026139, compound

Reagents, catalysts & solvents 1

HCID 65741,1,2-TrichloroethaneSolvent

Procedure

16.1 g (0.1 mol) of 6-chloromethyl-uracil and 57.0 g (0.3 mol) of triethyloxonium tetrafluoroborate are suspended in 100 ml of 1,1,2-trichloroethane and the suspension is left at 90° C. for 18 hours. The mixture is subsequently cooled and treated dropwise with a 50% aqueous solution of 41.5 g (0.3 mol) of potassium carbonate, incipient strong evolution of carbon dioxide being observed. The supernatant is then decanted off from the precipitated sludge-like residue and the residue is extracted several times with small amounts of methylene chloride. The combined organic phases are washed with water, dried over anhydrous sodium sulphate and evaporated under reduced pressure. The crude product is taken up in hot n-hexane and the solution is treated with active carbon and separated from insoluble constituents by filtration. Upon concentration of the filtrate there is obtained 4-chloromethyl-2,6-diethoxy-pyrimidine, m.p. 38°-39° C.

Workup

  1. temperatureThe mixture is subsequently cooled
  2. customThe supernatant is then decanted off from the precipitated sludge-like residue
  3. extractionthe residue is extracted several times with small amounts of methylene chloride
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated under reduced pressure
  7. additionthe solution is treated with active carbon
  8. customseparated from insoluble constituents by filtration

Sources & evidence

ORD record
ord-3971d8b3e1c84c05a0c59a96e495bc32
Source dataset
uspto-grants-1986_04
Patent number
US04584295

Reaction notes

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