Potassium Carbonate → 4-(2-Butynyloxy)-6-(2,6-dichloro-4-fluorophenoxy)pyrimidine

HRID 1759935

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+].[Cl:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([Cl:27])[C:21]=1[OH:28].[Cl-].[NH4+]>CN(C)C=O>[CH2:9]([O:8][C:6]1[CH:7]=[C:2]([O:28][C:21]2[C:20]([Cl:19])=[CH:25][C:24]([F:26])=[CH:23][C:22]=2[Cl:27])[N:3]=[CH:4][N:5]=1)[C:10]#[C:11][CH3:12]

Participants

Conditions

Temperature: 80 °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 0.20 g of 2,6-dichloro-4-fluorophenol, followed by stirring at 80° 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 0.22 g of 4-(2-butynyloxy)-6-(2,6-dichloro-4-fluorophenoxy)pyrimidine (the present compound (160)).

Workup

waitThe reaction mixture was then left
temperaturefor cooling to room temperature
extractionwas extracted three times with chloroform
washwashed with diluted hydrochloric acid
dry with materialwith water, and dried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-510097ca8d5b4f92b1b4b3e48fd49b98
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06838463B2

Linked notes

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