Dimethyl Sulfoxide → HCID 22599864, compound

HRID 1759894Notes

Reaction equation

HRID 1759894 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+].[CH:23]([NH2:26])([CH3:25])[CH3:24]>COC(C)(C)C>[CH2:13]([O:12][C:10]1[CH:11]=[C:6]([NH:26][CH:23]([CH3:25])[CH3:24])[N:7]=[CH:8][N:9]=1)[C:14]#[C:15][CH3:16]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6363IsopropylamineHCID 11430Potassium CarbonateHCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 22599864HCID 22599864, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
70 °C

Procedure

To 4 ml of dimethylsulfoxide were added 365 mg of 4-chloro-6-(2-butynyloxy)pyrimidine, 332 mg of potassium carbonate, and 591 mg of isopropylamine, followed by stirring at 70° C. for 6 hours. The reaction mixture was then left for cooling to room temperature, diluted with tert-butyl methyl ether, 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 339 mg of 4-(2-butynyloxy)-6-(isopropylamino)pyrimidine (the present compound (106)).

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-2820009f94ff4106b30c88495a1ed21a
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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