Potassium Carbonate → 4-(2-Butynyloxy)-6-(2,3-difluorophenoxy)pyrimidine

HRID 1759828

Reaction equation

HRID 1759828 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+].[F:19][C:20]1[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=1[OH:27].[Cl-].[NH4+]>CN(C)C=O>[CH2:9]([O:8][C:6]1[CH:7]=[C:2]([O:27][C:21]2[CH:22]=[CH:23][CH:24]=[C:25]([F:26])[C:20]=2[F:19])[N:3]=[CH:4][N:5]=1)[C:10]#[C:11][CH3:12]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 808792,3-DifluorophenolHCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 225997294-(2-Butynyloxy)-6-(2,3-difluorophenoxy)pyrimidineYield 56.2%

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 0.17 g of 2,3-difluorophenol, 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, and dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 0.17 g of 4-(2-butynyloxy)-6-(2,3-difluorophenoxy)pyrimidine (the present compound (39)).

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 materialwith water, and dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-de704a130de44c2e86846c8caf34db25
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Linked notes

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