2,3-Dichlorophenol → 4-(2,3-Dichlorophenoxy)-6-(2-propynyloxy)pyrimidine

HRID 1592094Notes

Reaction equation

HRID 1592094 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+].[Cl:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[OH:26].[Cl-].[NH4+]>CN(C)C=O>[Cl:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][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 113342,3-DichlorophenolHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 121375984-Chloro-6-(prop-2-yn-1-yloxy)pyrimidine

Product 1

HCID 225998414-(2,3-Dichlorophenoxy)-6-(2-propynyloxy)pyrimidineYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 5 ml of N,N-dimethylformamide were added 0.2 g of 4-chloro-6-(2-propynyloxy)pyrimidine, 0.25 g of potassium carbonate, and 0.21 g of 2,3-dichlorophenol, 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 0.25 g of 4-(2,3-dichlorophenoxy)-6-(2-propynyloxy)pyrimidine (the present compound (26)), m.p.: 91.9° 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-b7a8af17075f4708b3ecd573415e7968
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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