HCID 13304947, compound → HCID 13304948, compound

HRID 371395Notes

Reaction equation

HRID 371395 reaction equation
[CH2:1]([C:3]1[C:4]([O:15][CH3:16])=[N:5][C:6]2[N:7]([CH:10]=[C:11]([CH2:13][OH:14])[N:12]=2)[C:8]=1[CH3:9])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([C:3]1[C:4]([O:15][CH3:16])=[N:5][C:6]2[N:7]([CH:10]=[C:11]([CH:13]=[O:14])[N:12]=2)[C:8]=1[CH3:9])[CH3:2]

Participants

4

Reactant 1

HCID 13304947HCID 13304947, compound

Product 1

HCID 13304948HCID 13304948, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 15.25 g (69 mmol) of 6-ethyl-7-methoxy-5-methylimidazo-[1,2-a]pyrimidin-2-yl methanol in 200 ml of chloroform was added 40 g of activated manganese dioxide and the stirred mixture was refluxed for 18 hours. A further 20 g of the oxidizing agent were added and the mixture was refluxed for a further 4 hours. The cooled mixture was filtered through celite and the filtrate was evaporated to obtain 10.9 g (72% yield) of 6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidine-2-carboxaldehyde as a white crystalline solid melting at 185°-186° C.

Workup

  1. temperaturethe stirred mixture was refluxed for 18 hours
  2. additionA further 20 g of the oxidizing agent were added
  3. temperaturethe mixture was refluxed for a further 4 hours
  4. filtrationThe cooled mixture was filtered through celite
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-843659cbab024171b80c35c659ae6cea
Source dataset
uspto-grants-1985_07
Patent number
US04532243

Reaction notes

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