Water → HCID 54343679, compound

HRID 1982707Notes

Reaction equation

HRID 1982707 reaction equation
[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:5]=1)=[O:2].[Se](=O)=O.O.[C:20](=[O:23])(O)[O-].[Na+].C[N:26](C)C=O>>[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10](=[N:26][O:23][CH3:20])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:5]=1)=[O:2]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24007Selenium DioxideHCID 516892Sodium BicarbonateHCID 13060219HCID 13060219, compound

Product 1

HCID 54343679HCID 54343679, compound

Procedure

A mixture of ethyl 2-(4-formamidopyrimidine-2-yl)acetate (50.0 g) and selenium dioxide (31.87 g) in N,N-dimethylformamide (240 ml) was stirred for an hour at 70° to 75° C. and cooled to ambient temperature. The precipitated solid was filtered off and the filtrate was evaporated in vacuo to give an oily product. The oil was added to water (750 ml) under stirring, adjusting to pH7 with an aqueous solution of sodium bicarbonate. The precipitated yellow substance was filtered off and washed with water. The filtrate and washings were combined and thereto was added methoxyamine hydrochloride (19.95 g). The mixture was adjusted to pH4 with an aqueous solution of sodium bicarbonate and stirred for 3 hours at ambient temperature. The aqueous reaction mixture was extracted with ethyl acetate and the extract was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and evaporated to give ethyl 2-(4-formamidopyrimidin-2-yl)-2-methoxyiminoacetate (syn isomer) (31 g) as a brownish oil.

Workup

  1. filtrationThe precipitated solid was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customto give an oily product
  4. stirringunder stirring
  5. filtrationThe precipitated yellow substance was filtered off
  6. washwashed with water
  7. additionwas added methoxyamine hydrochloride (19.95 g)
  8. stirringstirred for 3 hours at ambient temperature
  9. extractionThe aqueous reaction mixture was extracted with ethyl acetate
  10. washthe extract was washed with an aqueous solution of sodium chloride
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customevaporated

Sources & evidence

ORD record
ord-4d19ca9e94414071b7ea53c150187153
Source dataset
uspto-grants-1986_06
Patent number
US04596869

Reaction notes

Loading…