Ethanol → 2-(4-Fluorophenyl)pyrimidine-5-carbaldehyde

HRID 1873768Notes

Reaction equation

HRID 1873768 reaction equation
Cl.[F:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][CH:4]=1.[CH3:12][C:13]([O-])([CH3:15])[CH3:14].[K+].C([OH:20])C>>[F:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]2[N:9]=[CH:14][C:13]([CH:15]=[O:20])=[CH:12][N:8]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 124561604-Fluorobenzamidine HydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 140084722-(4-Fluorophenyl)pyrimidine-5-carbaldehyde

Procedure

2 g (11.45 mmol) of 4-fluorobenzamidine hydrochloride, 4.09 g (11.45 mmol) of 2-dimethylaminomethylene-1,3-bis(dimethylimmonio)propane-bis(tetrafluoroborate) and 3.86 g (34.36 mmol) of potassium tert-butylate in 70 ml of ethanol were heated under reflux for 8 h. After concentration, water and ethyl acetate were added. The organic phase was washed with a potassium hydrogensulfate solution and water, dried and evaporated. Yield: 1.87 g.

Workup

  1. temperatureunder reflux for 8 h
  2. concentrationAfter concentration, water and ethyl acetate
  3. additionwere added
  4. washThe organic phase was washed with a potassium hydrogensulfate solution and water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-47cf127e15fa4ed292425bcae8ddc936
Source dataset
uspto-grants-2012_11
Patent number
US08304438B2

Reaction notes

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