Acetone → 4,6-Dichloro-5-pyrimidinecarbaldehyde

HRID 419723Notes

Reaction equation

HRID 419723 reaction equation
CN(C=O)C.O=P(Cl)(Cl)[Cl:8].[OH:11][C:12]1[CH:17]=[C:16](O)[N:15]=[CH:14][N:13]=1.CC(C)=O.[CH2:23]([Cl:25])Cl>>[Cl:8][C:16]1[C:17]([CH:12]=[O:11])=[C:23]([Cl:25])[N:13]=[CH:14][N:15]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 178516651HCID 178516651, compound

Product 1

HCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde

Conditions

Temperature
0 °C

Procedure

Charge DMF (8.9 mL, 1.3 eq) in a round bottom flask and cool to 0° C. Add POCl3 (32.6 mL, 4.0 eq) to the reaction drop wise at 0° C. Stir the reaction mass at 0° C. for 1 h. Charge 4,6-dihydroxy pyrimidine (10.0 g, 1.0 eq) to the reaction mass and allowed it to come to room temperature slowly. Reflux the reaction mass for 4 h and monitor the reaction by TLC (10% acetone in DCM). Concentrate the reaction mass under vacuum and pour the concentrated reaction mass over crushed ice. Extract the product with diethyl ether and wash with saturated aq. sodium chloride. Dry the organic layer over anhydrous sodium sulfate and concentrate it under vacuum to get pale yellow solid as product (6.2 g, 40%).

Workup

  1. customwise at 0° C
  2. customto come to room temperature
  3. temperatureReflux the reaction mass for 4 h
  4. concentrationConcentrate the reaction mass under vacuum
  5. additionpour
  6. customthe concentrated reaction mass
  7. customover crushed ice
  8. extractionExtract the product with diethyl ether
  9. washwash with saturated aq. sodium chloride
  10. dry with materialDry the organic layer over anhydrous sodium sulfate
  11. concentrationconcentrate it under vacuum
  12. customto get pale yellow solid as product (6.2 g, 40%)

Sources & evidence

ORD record
ord-86a1070773684933b332ee8f1c4179f8
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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