Ethyl Acetate → HCID 13060175, compound

HRID 1982686Notes

Reaction equation

HRID 1982686 reaction equation
[Se]=O.[CH:3]([NH:5][C:6]1[N:11]=[C:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:8][N:7]=1)=[O:4].C(OCC)(=[O:19])C>O1CCOCC1>[CH:3]([NH:5][C:6]1[N:11]=[C:10]([C:12](=[O:19])[C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:8][N:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 167175OxyselenideHCID 13060169HCID 13060169, compound

Product 1

HCID 13060175HCID 13060175, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Selenium oxide (9.92 g.) was added to a solution of methyl 2-(2-formamidopyrimidin-4-yl)acetate (14.52 g.) in dioxane (200 ml.) at 90° to 95° C. over 20 minutes, and stirred at the same temperature for an hour. After cooling the resultant solution, the solution was filtered through a column packed with silica gel (20 g.), washed with dioxane and concentrated under reduced pressure. The residue was dissolved in acetone and filtered, and then the filtrate was concentrated under reduced pressure. The residue was triturated with chloroform to give a crude product (8.2 g.). The product was added to ethyl acetate, heated and an insoluble material was filtered out. The filtrate was cooled, and the precipitates were collected by filtration to give methyl 2-(2-formamidopyrimidin-4-yl)glyoxylate (5.55 g.). The product was recrystallized from ethyl acetate (saturated with water) to give mono hydrate thereof, mp 143° to 144° C.

Workup

  1. filtrationthe solution was filtered through a column
  2. washwashed with dioxane
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in acetone
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was triturated with chloroform
  8. customto give a crude product (8.2 g.)
  9. temperatureheated
  10. filtrationan insoluble material was filtered out
  11. temperatureThe filtrate was cooled
  12. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-a90dd3d98f70413bac5ab710f7ca4f2c
Source dataset
uspto-grants-1986_06
Patent number
US04596869

Reaction notes

Loading…