Dimethylformamide dimethyl acetal → (4-Chlorophenyl)(pyrimidin-5-yl)methanone

HRID 986466Notes

Reaction equation

HRID 986466 reaction equation
COC(OC)[N:4]([CH3:6])[CH3:5].O[CH:10]=[CH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[O:13].C(O)(=O)C.C(N)=[NH:26].C[O-].[Na+]>C1(C)C=CC=CC=1.C(O)C.O>[N:4]1[CH:5]=[C:11]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[O:13])[CH:10]=[N:26][CH:6]=1

Participants

8

Reactant 4

HCID 78373Dimethylformamide dimethyl acetalHCID 160693Formamidine acetateHCID 3456926HCID 3456926, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 13645652(4-Chlorophenyl)(pyrimidin-5-yl)methanoneYield 31%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

7.7 g (0.065 mole) of N,N-dimethylformamide dimethyl acetal are added in portions to 10 g (0.055 mole) of 4-chlorophenyl hydroxyvinyl ketone (compare 1st stage) in 10 ml of toluene at 0° C. The reaction mixture is subsequently stirred for 15 minutes, and 5.7 g (0.055 mole) of formamidine acetate are then added. After further subsequent stirring for 15 minutes, a solution of 3 g (0.055 mole) of sodium methylate in 80 ml of ethanol is added dropwise and the mixture is subsequently stirred under reflux for 8 hours. The reaction mixture is allowed to cool and is poured onto 400 ml of water and extracted with toluene. The organic phase is washed with water, dried over sodium sulphate and concentrated. The residue is purified by column chromatography (ethyl acetate: cyclohexane =3:1; silica gel). 3.7 g (31% of theory) of 4-chlorophenyl 5-pyrimidinyl ketone of melting point 110°-112° C. are obtained.

Workup

  1. stirringAfter further subsequent stirring for 15 minutes
  2. stirringthe mixture is subsequently stirred
  3. temperatureunder reflux for 8 hours
  4. temperatureto cool
  5. extractionextracted with toluene
  6. washThe organic phase is washed with water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. customThe residue is purified by column chromatography (ethyl acetate: cyclohexane =3:1; silica gel)

Sources & evidence

ORD record
ord-a30ff64c31cb42599a499bc964a81b67
Source dataset
uspto-grants-1987_12
Patent number
US04713456

Reaction notes

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