Dimethyl Sulfoxide → HCID 22599898, compound

HRID 1759902Notes

Reaction equation

HRID 1759902 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+].[CH2:23]([NH:26][CH2:27][CH2:28][CH3:29])[CH2:24][CH3:25]>C(OCC)(=O)C>[CH2:13]([O:12][C:10]1[CH:11]=[C:6]([N:26]([CH2:27][CH2:28][CH3:29])[CH2:23][CH2:24][CH3:25])[N:7]=[CH:8][N:9]=1)[C:14]#[C:15][CH3:16]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8902DipropylamineHCID 11430Potassium CarbonateHCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 22599898HCID 22599898, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To 2 ml of dimethylsulfoxide were added 183 mg of 4-chloro-6-(2-butynyloxy)pyrimidine, 166 mg of potassium carbonate, and 152 mg of dipropylamine, followed by stirring at 80° C. for 8 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 thin layer chromatography to give 179 mg of 4-(2-butynyloxy)-6-(dipropylamino)pyrimidine (the present compound (113)).

Workup

  1. waitThe reaction mixture was then left
  2. temperaturefor cooling to room temperature
  3. washwashed twice with an aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-312e255368844bf7941f777691e1264e
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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