Dimethyl Sulfoxide → HCID 22599716, compound

HRID 1759900Notes

Reaction equation

HRID 1759900 reaction equation
CS(C)=O.Cl[C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]#[C:15][CH3:16])[N:9]=[CH:8][N:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:23][C:24]([F:31])([C:27]([F:30])([F:29])[F:28])[CH2:25][NH2:26]>C(OCC)(=O)C>[CH2:13]([O:12][C:10]1[CH:11]=[C:6]([NH:26][CH2:25][C:24]([F:31])([F:23])[C:27]([F:30])([F:29])[F:28])[N:7]=[CH:8][N:9]=1)[C:14]#[C:15][CH3:16]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 790022,2,3,3,3-Pentafluoropropylamine2×HCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 22599716HCID 22599716, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To 4 ml of dimethylsulfoxide were added 365 mg of 4-chloro-6-(2-butynyloxy)pyrimidine, 442 mg of potassium carbonate, and 495 mg of 2,2,3,3,3-pentafluoropropylamine, followed by stirring at 80° C. for 4 hours. Then, 596 mg of 2,2,3,3,3-pentafluoropropylamine was further added, and the mixture was stirred at 100° C. for 6 hours. The reaction mixture was then left for cooling to room temperature, diluted with ethyl acetate, and washed twice with an aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 73 mg of 4-(2-butynyloxy)-6-(2,2,3,3,3-pentafluoropropylamino)pyrimidine (the present compound (111)).

Workup

  1. stirringthe mixture was stirred at 100° C. for 6 hours
  2. waitThe reaction mixture was then left
  3. temperaturefor cooling to room temperature
  4. washwashed twice with an aqueous sodium chloride solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4ed581aa5845465f9ebafaab19111087
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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