Dimethylformamide → 4(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-

HRID 2245254Notes

Reaction equation

HRID 2245254 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN(C)C=O.S[C:12]1[N:17]([CH3:18])[C:16](=[O:19])[CH:15]=[C:14]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[N:13]=1>C(OCC)(=O)C>[Cl:3][C:12]1[N:17]([CH3:18])[C:16](=[O:19])[CH:15]=[C:14]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[N:13]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178481674HCID 178481674, compound

Product 1

HCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-Yield 77.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Phosphorous oxychloride (26.11 g, 170 mmol) was added to dimethylformamide (180 ml) and stirred 20 min. 2-mercapto-3-methyl-6-(4-pyridyl)-pyrimidine-4-one (24.15 g, 110 mmol) was added to the solution and stirred 5 min and then stirred at 70° C. for 2 hours. Ethyl acetate (630 ml) was added to the ice-cooled solution and precipitate was collected by filtration after 20 minutes stirring. After drying, the precipitate was dissolved in water (400 ml) and pH was adjusted to 10 by aqueous sodium hydroxide. The precipitate was washed with water, filtered and dried to give the title compound (18.82 g, 77%).

Workup

  1. stirringstirred 5 min
  2. stirringstirred at 70° C. for 2 hours
  3. temperaturecooled solution and precipitate
  4. filtrationwas collected by filtration after 20 minutes
  5. stirringstirring
  6. customAfter drying
  7. dissolutionthe precipitate was dissolved in water (400 ml)
  8. washThe precipitate was washed with water
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-ad26d265c8cc476bb073822cf1936487
Source dataset
uspto-grants-2010_03
Patent number
US07683069B2

Reaction notes

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