Potassium Carbonate → HCID 67441231, compound

HRID 1517251Notes

Reaction equation

HRID 1517251 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([NH:14][O:15][CH3:16])=[O:13].Cl[C:18]1[C:23]([CH:24]=O)=[CH:22][N:21]=[C:20]([S:26][CH3:27])[N:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]1[C:12](=[O:13])[N:14]([O:15][CH3:16])[C:18]2[N:19]=[C:20]([S:26][CH3:27])[N:21]=[CH:22][C:23]=2[CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 594193864-Chloro-2-(methylsulfanyl)pyrimidine-5-carbaldehydeHCID 86658578HCID 86658578, compound

Product 1

HCID 67441231HCID 67441231, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-Chloro-4-nitrophenyl)-N-methoxyacetamide (49.3 mmol) and 4-chloro-2-(methylthio)pyrimidine-5-carbaldehyde (41.2 mmol) were dissolved in DMF (600 mL). The solution was cooled to 0° C., and K2CO3 (91 mmol) was added in one poroom temperatureion. The mixture was stirred at 0° C. for 2 h and then at room temperature for 48 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to 60 mL. Water (600 mL) was added. The precipitate was filtered, washed twice with EtOH and dried. The by-product (Z) -6-(2-chloro-4-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-4-nitrophenyl)-8-methoxy-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one as a solid (63%).

Workup

  1. waitat room temperature for 48 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure to 60 mL
  4. additionWater (600 mL) was added
  5. filtrationThe precipitate was filtered
  6. washwashed twice with EtOH
  7. customdried
  8. customThe by-product (Z) -6-(2-chloro-4-nitrophenyl)-2-(methylthio)-7H-pyrano[2,3-d]pyrimidin-7-one O-methyl oxime was separated
  9. temperatureby reflux of the mixture for 4 h in EtOH
  10. filtrationhot filtration of the suspension through a sintered glass funnel
  11. customEvaporation of the filtrate
  12. customdrying

Sources & evidence

ORD record
ord-4d9e79641b1a4d0f895c0c1c5b1d036f
Source dataset
uspto-grants-2012_07
Patent number
US08232283B2

Reaction notes

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