2,3-Dimethylphenol → HCID 22599878, compound

HRID 1759856Notes

Reaction equation

HRID 1759856 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]#[C:11][CH3:12])[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[OH:27].[Cl-].[NH4+]>CN(C)C=O>[CH3:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[O:27][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]#[C:11][CH3:12])[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 106872,3-DimethylphenolHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 22599878HCID 22599878, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 2 ml of N,N-dimethylformamide were added 0.2 g of 4-chloro-6-(2-butynyloxy)pyrimidine, 0.23 g of potassium carbonate, and 0.16 g of 2,3-dimethylphenol, followed by stirring at 60° C. for 7 hours. The reaction mixture was then left for cooling to room temperature and poured into a saturated aqueous ammonium chloride solution, which was extracted three times with chloroform. The chloroform layers were combined, washed with diluted hydrochloric acid and then with water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 0.26 g of 4-(2,3-dimethylphenoxy)-6-(2-butynyloxy)pyrimidine (the present compound (67)).

Workup

  1. waitThe reaction mixture was then left
  2. temperaturefor cooling to room temperature
  3. extractionwas extracted three times with chloroform
  4. washwashed with diluted hydrochloric acid
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-23417b4c07ed435e8f958a623b4c64cb
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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