Formamide → HCID 135704063, compound

HRID 651419Notes

Reaction equation

HRID 651419 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)=O)C.C([O-])(=O)C.[NH4+:24].[CH:25]([NH2:27])=O.CC(C)([O-])C.[K+]>C(O)C.C(O)(=O)C>[F:16][C:15]([F:18])([F:17])[C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[CH2:8][C:6]1[N:27]=[CH:25][NH:24][C:4](=[O:3])[CH:5]=1

Participants

7

Reactant 4

HCID 713FormamideHCID 517165Ammonium AcetateHCID 23665647Potassium tert-butoxideHCID 45156320HCID 45156320, compound

Product 1

HCID 135704063HCID 135704063, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl-(3-trifluoromethylphenyl)acetoacetate (15.3 g, 0.056 mol) is added to a solution of ammonium acetate (21.6 g, 0.28 mol) in ethanol (100 ml) and the mixture is refluxed for 3 hours. The solution is concentrated under reduced pressure and then suspended in ethyl acetate. The suspension is washed with water and saturated brine and the organic layer concentrated. The material is then dissolved in dimethylsulfoxide (125 ml) and formamide (20 ml) and potassium tert-butoxide (1.28 g, 0.011 mol) are added. The solution is heated for 18 hours at 100° C. Upon cooling the solution is poured into ice (1000 ml) and glacial acetic acid (20 ml). The resulting solid is collected and air dried. The material is then triturated with diethyl ether and is air dried to give 6-(3-trifluoromethylbenzyl)pyrimidin-4-one (7.20 g).

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. concentrationThe solution is concentrated under reduced pressure
  3. washThe suspension is washed with water and saturated brine
  4. concentrationthe organic layer concentrated
  5. dissolutionThe material is then dissolved in dimethylsulfoxide (125 ml)
  6. temperatureUpon cooling the solution
  7. customThe resulting solid is collected
  8. customair dried
  9. customThe material is then triturated with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-09366f1604d544b7ada76a226a4215ab
Source dataset
uspto-grants-2001_08
Patent number
US06281219B1

Reaction notes

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