Dimethyl Sulfoxide → HCID 22599898, compound

HRID 1592180Notes

Reaction equation

HRID 1592180 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-d10266ee435043fc8c86a9be38e47519
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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