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Potassium Carbonate → 2-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-one

HRID 515440
Notes
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Reaction equation

HRID 515440 reaction equation
P(Cl)(Cl)([Cl:3])=O.S[C:7]1[N:12]([CH3:13])[C:11](=[O:14])[CH:10]=[C:9]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][N:16]=2)[N:8]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:3][C:7]1[N:12]([CH3:13])[C:11](=[O:14])[CH:10]=[C:9]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][N:16]=2)[N:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 1784816782-Mercapto-3-methyl-6-(pyrimidin-4-YL)-3H-pyrimidin-4-one

Product 1

HCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-oneYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Phosphorous oxychloride (4.60 g, 30 mmol) was added to dimethylformamide (32 ml) and stirred for 20 min at 0° C. 2-Mercapto-3-methyl-6-(4-pyrimidyl)-3H-pyrimidine-4-one (4.40 g, 20 mmol) was added to the solution and stirred 5 min and then stirred at 70° C. for 2 hours. The reaction mixture was poured into ice water, neutralized by solid potassium carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated under reduced pressure. Purification of the residue by silica gel chromatography (ethyl acetate) gave the title compound (1.20 g, 27%).

Workup

  1. stirringstirred 5 min
  2. stirringstirred at 70° C. for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customPurification of the residue by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-5513844a4bd644299a40f181975373a6
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09108957B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes