HCID 59311650, compound → HCID 59311412, compound

HRID 1693281Notes

Reaction equation

HRID 1693281 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([OH:14])[CH2:10][CH2:11][CH:12]=[CH2:13])=[C:4]([Cl:15])[N:3]=1>[O-2].[O-2].[Mn+4].ClCCCl>[NH2:1][C:2]1[N:3]=[C:4]([Cl:15])[C:5]([C:9](=[O:14])[CH2:10][CH2:11][CH:12]=[CH2:13])=[C:6]([Cl:8])[N:7]=1

Participants

4

Reactant 1

HCID 59311650HCID 59311650, compound

Product 1

HCID 59311412HCID 59311412, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A mixture composed of the above crude 1-(2-amino-4,6-dichloropyrimidin-5-yl)pent-4-en-1-ol (5.06 g), 1,2-dichloroethane (300 mL) and manganese dioxide (20.15 g) was heated under reflux for 15 hours. After confirming that the raw material disappeared, the reaction solution was filtered through Celite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-chloroform) to obtain the title compound (1.22 g, 24.3%) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. filtrationthe reaction solution was filtered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-chloroform)

Sources & evidence

ORD record
ord-34ad84f9b5734762ab8a18a170c73ff9
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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