Potassium Carbonate → 4-(2,6-Difluorophenoxy)-6-(2-propynyloxy)pyrimidine

HRID 1759810Notes

Reaction equation

HRID 1759810 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]#[CH:11])[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[OH:26].[Cl-].[NH4+]>CN(C)C=O>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[O:26][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]#[CH:11])[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 943922,6-DifluorophenolHCID 121375984-Chloro-6-(prop-2-yn-1-yloxy)pyrimidine

Product 1

HCID 225997124-(2,6-Difluorophenoxy)-6-(2-propynyloxy)pyrimidineYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 5 ml of N,N-dimethylformamide were added 0.43 g of 4-chloro-6-(2-propynyloxy)pyrimidine, 0.52 g of potassium carbonate, and 0.4 g of 2,6-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 0.53 g of 4-(2,6-difluorophenoxy)-6-(2-propynyloxy)pyrimidine (the present compound (21)), m.p.: 67.2° C.

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-317673ee26fe4a8f8382d8f918d4220a
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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