Potassium Carbonate → 6-(2-chloro-5-nitrophenyl)-8-methoxy-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1517243Notes

Reaction equation

HRID 1517243 reaction equation
Cl[C:2]1[C:7]([CH:8]=O)=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=1[CH2:22][C:23]([NH:25][O:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=1[C:22]1[C:23](=[O:24])[N:25]([O:26][CH3:27])[C:2]2[N:3]=[C:4]([S:10][CH3:11])[N:5]=[CH:6][C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 594193864-Chloro-2-(methylsulfanyl)pyrimidine-5-carbaldehydeHCID 866585772-(2-chloro-5-nitrophenyl)-N-methoxyacetamide

Product 1

HCID 674406646-(2-chloro-5-nitrophenyl)-8-methoxy-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Chloro-2-(methylthio)pyrimidine-5-carbaldehyde (90 mmol) and 2-(2-chloro-5-nitrophenyl)-N-methoxyacetamide (98 mmol) were dissolved in DMF (1 L) to give a brown solution. The reaction mixture was cooled to 0° C. Potassium carbonate (197 mmol) was added. The mixture was stirred at 0° C. for 2 h and then allowed to warm to room temperature over night. Potassium carbonate was filtered off and the filtrate was concentrated to approximately 100 mL. The residue was diluted with water (1 L) and filtered. The filter cake was washed with 350 mL of EtOH to give a brown solid that was dried in vacuum. The by-product (Z)-6-(2-chloro-5-nitrophenyl)-2-(methylthio)-7H-pyrano[2,3-d]pyrimidin-7-one O-methyl oxime was separated by reflux of the mixture for 4 h in EtOH and hot filtration of the suspension through a sintered glass funnel. Evaporation of the filtrate and drying gave 6-(2-chloro-5-nitrophenyl)-8-methoxy-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one as a solid (52%).

Workup

  1. customto give a brown solution
  2. temperatureto warm to room temperature over night
  3. filtrationPotassium carbonate was filtered off
  4. concentrationthe filtrate was concentrated to approximately 100 mL
  5. additionThe residue was diluted with water (1 L)
  6. filtrationfiltered
  7. washThe filter cake was washed with 350 mL of EtOH
  8. customto give a brown solid that
  9. customwas dried in vacuum
  10. customThe by-product (Z)-6-(2-chloro-5-nitrophenyl)-2-(methylthio)-7H-pyrano[2,3-d]pyrimidin-7-one O-methyl oxime was separated
  11. temperatureby reflux of the mixture for 4 h in EtOH
  12. filtrationhot filtration of the suspension through a sintered glass funnel
  13. customEvaporation of the filtrate
  14. customdrying

Sources & evidence

ORD record
ord-facd37fbe5f04735842198e942e21462
Source dataset
uspto-grants-2012_07
Patent number
US08232283B2

Reaction notes

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