HCID 13304949, compound → HCID 13304950, compound

HRID 280089Notes

Reaction equation

HRID 280089 reaction equation
[CH2:1]([C:3]1[C:4]([O:23][CH3:24])=[N:5][C:6]2[N:7]([CH:10]=[C:11]([CH:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[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:23][CH3:24])=[N:5][C:6]2[N:7]([CH:10]=[C:11]([C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[O:14])[N:12]=2)[C:8]=1[CH3:9])[CH3:2]

Participants

4

Reactant 1

HCID 13304949HCID 13304949, compound

Product 1

HCID 13304950HCID 13304950, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

10 g of activated manganese dioxide were added to a solution of 2.2 g (6.7 mmol) of (6-ethyl-7-methoxy-5-methyl imidazo[1,2-a]pyrimidin-2-yl)(4-methoxyphenyl)methanol in 100 ml of chloroform and the mixture was stirred at room temperature for 18 hours. The mixture was filtered through celite and evaporation of the filtrate gave a solid product. Purification on a 100 g silica gel column using chloroform-methanol (98 to 2) as the eluant gave 1.3 g (59% yield) of pure (6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidin-2-yl)(4-methoxyphenyl)methanone as a white crystalline solid melting at 196°-7° C. Overall yield from ester was 37%.

Workup

  1. filtrationThe mixture was filtered through celite and evaporation of the filtrate
  2. customgave a solid product
  3. customPurification on a 100 g silica gel column

Sources & evidence

ORD record
ord-db9a1e1eacff40158bdf412d804ed2ab
Source dataset
uspto-grants-1986_05
Patent number
US04588720

Reaction notes

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