Potassium Carbonate → HCID 22599814, compound

HRID 1592120Notes

Reaction equation

HRID 1592120 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[CH:21]=[C:22]([OH:27])[CH:23]=[CH:24][C:25]=1[F:26].[Cl-].[NH4+]>CN(C)C=O>[CH2:9]([O:8][C:6]1[CH:7]=[C:2]([O:27][C:22]2[CH:23]=[CH:24][C:25]([F:26])=[C:20]([F:19])[CH:21]=2)[N:3]=[CH:4][N:5]=1)[C:10]#[C:11][CH3:12]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 759273,4-DifluorophenolHCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 22599814HCID 22599814, compoundYield 66.1%

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 3,4-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 0.2 g of 4-(2-butynyloxy)-6-(3,4-difluorophenoxy)pyrimidine (the present compound (10)), m.p.: 109.7° 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-ef88ac89f66a470784336d1c9f45eef1
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

Loading…