Toluene → HCID 68006952, compound

HRID 1027790Notes

Reaction equation

HRID 1027790 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]([C:13]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:14])[C:7](=[O:12])[N:8]2[CH3:11])=[CH:4][N:3]=1.[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C(O)C>[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:2]1[N:10]=[C:9]2[C:5]([N:6]([C:13]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:14])[C:7](=[O:12])[N:8]2[CH3:11])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 86667461HCID 86667461, compound

Product 1

HCID 68006952HCID 68006952, compound

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

To a mixture of 2-chloro-9-methyl-7-(pyrrolidin-1-ylcarbonyl)-7,9-dihydro-8H-purine-8-one <the compound of Reference Example 16> (100 mg), 2-fluorophenylboronic acid (74 mg), potassium carbonate (145 mg), toluene (3 ml) and ethanol (1 ml) was added bis(tri-tert-butylphosphine)palladium (9 mg) under nitrogen atmosphere and the mixture was stirred at 130° C. under microwave irradiation for 1 hour. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: chloroform/methanol=100/0˜90/10) to give the title compound 58 mg.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (eluent: chloroform/methanol=100/0˜90/10)

Sources & evidence

ORD record
ord-5017637e1a1c4ea0a9eff95e6bf7a8ee
Source dataset
uspto-grants-2014_05
Patent number
US08735406B2

Reaction notes

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