Dimethyl Sulfoxide → HCID 22599788, compound

HRID 1592174Notes

Reaction equation

HRID 1592174 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]([NH2:25])[CH3:24]>COC(C)(C)C>[CH2:13]([O:12][C:10]1[CH:11]=[C:6]([NH:25][CH2:23][CH3:24])[N:7]=[CH:8][N:9]=1)[C:14]#[C:15][CH3:16]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6341EthylamineHCID 11430Potassium CarbonateHCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 22599788HCID 22599788, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
50 °C

Procedure

To 20 ml of dimethylsulfoxide were added 1.83 g of 4-chloro-6-(2-butynyloxy)pyrimidine, 2.20 g of potassium carbonate, and 20 ml of ethylamine (2.0 M tetrahydrofuran solution), followed by stirring at 50° C. for 8 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 recrystallized from tert-butyl methyl ether to give 1.14 g of 4-(2-butynyloxy)-6-(ethylamino)pyrimidine (the present compound (108)).

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
  6. customThe residue was recrystallized from tert-butyl methyl ether

Sources & evidence

ORD record
ord-746625dd078e486d9c07537ab44737a0
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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