Sodium ethoxide → HCID 22744085, compound

HRID 1978978Notes

Reaction equation

HRID 1978978 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[C:8]([C:9]([O:11]CC)=O)=[CH:7][N:6]=[CH:5][N:4]=1.[C:16](=[N:21]O)([NH2:20])[CH:17]([CH3:19])[CH3:18].[O-]CC.[Na+]>C(O)C>[CH:17]([C:16]1[N:21]=[C:9]([C:8]2[C:3]([C:2]([F:1])([F:14])[F:15])=[N:4][CH:5]=[N:6][CH:7]=2)[O:11][N:20]=1)([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 2794833N'-Hydroxy-2-methylpropanimidamideHCID 22744070Ethyl 4-(trifluoromethyl)pyrimidine-5-carboxylate

Product 1

HCID 22744085HCID 22744085, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

2 g of ethyl 4-trifluoromethylpyrimidine-5-carboxylate and 1.56 g of isobutyramide oxime were initially charged in 15 ml of ethanol and cooled to 0° C. 10 ml of a 1.2 molar sodium ethoxide solution were added dropwise to this solution. The mixture was allowed to warm to room temperature over a period of one hour and then heated under reflux until the reaction, according to TLC, had ended. The reaction mixture was concentrated and the residue was taken up in saturated ammonium chloride solution and extracted with diethyl ether. Chromatographic purification of the crude product gave the desired compound as a yellowish oil.

Workup

  1. temperatureto warm to room temperature over a period of one hour
  2. temperatureheated
  3. temperatureunder reflux until the reaction
  4. concentrationThe reaction mixture was concentrated
  5. extractionextracted with diethyl ether
  6. customChromatographic purification of the crude product

Sources & evidence

ORD record
ord-4f98300ffe5041089e284431e232ce91
Source dataset
uspto-grants-2001_05
Patent number
US06239160B1

Reaction notes

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