Ethanol → HCID 44479178, compound

HRID 1505490Notes

Reaction equation

Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1.[F:17][C:18]1[C:23](B(O)O)=[CH:22][CH:21]=[CH:20][N:19]=1.C([O-])(=O)C.[K+].C(O)C>O>[F:17][C:18]1[C:23]([C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (239 mg, 1 mmol) prepared at Step 6, 2-fluoropyridin-3-yl boronic acid (189 mg, 1.3 mmol), potassium acetate (216 mg, 2.2 mmol), and bis(di-tert-butyl-(4-dimethyl amino phenyl) phosphine)dichloropalladium (14 mg, 0.02 mmol) were added into a mixed solvent of ethanol and water (5/1). The reactant was refluxed and stirred under nitrogen pressure at 80° C. for 2 hours. After the reaction, the solution was concentrated and washed with water and salt water, and then extracted with ethylacetate. After drying the organic layer with sulfuric anhydride magnesium and vacuum concentrating, the residuals were refined by means of column chromatography, so that 279 mg of the target compound, 6-(2-fluoropyridin-3-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (percentage yield: 93%), was obtained.

Workup

temperatureThe reactant was refluxed
customAfter the reaction
concentrationthe solution was concentrated
washwashed with water and salt water
extractionextracted with ethylacetate
dry with materialAfter drying the organic layer with sulfuric anhydride magnesium and vacuum
concentrationconcentrating

Sources & evidence

ORD record: ord-6bd56993f3be444eab7adbecabeb8ce9
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216981B2

Reaction notes

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