Dimethylformamide → HCID 86698982, compound

HRID 539892Notes

Reaction equation

HRID 539892 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([CH:8]=[O:9])[C:5]([CH:10]2[CH2:12][CH2:11]2)=[N:4]1)[CH3:2].[C:13](=[O:16])([O-])[O-].[K+].[K+].[Cl:19][C:20]1[N:25]=C(Cl)C=[CH:22][N:21]=1.[CH3:27]N(C)C=O>>[Cl:19][C:20]1[N:25]=[C:1]([N:3]2[CH:7]=[C:6]([C:8]([O:16][CH2:13][CH3:27])=[O:9])[C:5]([CH:10]3[CH2:11][CH2:12]3)=[N:4]2)[CH:2]=[CH:22][N:21]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 775312,4-DichloropyrimidineHCID 196213603-Cyclopropyl-1-ethyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 86698982HCID 86698982, compoundYield 68%

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 3-cyclopropyl-1H-pyrazole-4-carbaldehyde (5.4 g, 30.0 mmol) in 100 mL of anhydrous N,N-dimethylformamide were added potassium carbonate (10.4 g, 75 mmol) and 2,4-dichloropyrimidine (7.1 g, 30.0 mmol) at room temperature. The resulting suspension was stirred for 6 hours at 60° C. with monitoring a reaction with LC-MS or thin layer chromatography (TLC). Volatiles were removed and the residue was extracted with dichloromethane. The collected organic layer was washed with brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting solid was recrystallized in acetonitrile to afford the desired intermediate 4 as a pale yellow solid (6.0 g, 68%); MS (ESI) m/z 293 [M+H]+.

Workup

  1. customa reaction with LC-MS or thin layer chromatography (TLC)
  2. customVolatiles were removed
  3. extractionthe residue was extracted with dichloromethane
  4. washThe collected organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was recrystallized in acetonitrile

Sources & evidence

ORD record
ord-582c27b75ca24b5baffdd26280f8fcc0
Source dataset
uspto-grants-2014_10
Patent number
US08871778B2

Reaction notes

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