2-Chloroquinoline-3-boronic acid → 2-Chloro-3-(2-methyl-9-(tetrahydro-2H-pyran-2-YL)-9H-purin-6-YL)quinoline

HRID 1811909Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1.[Cl:18][C:19]1[C:28](B(O)O)=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:18][C:19]1[C:28]([C:2]2[N:10]=[C:9]([CH3:11])[N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6-chloro-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (0.55 g, 2.18 mmol), 2-chloroquinolin-3-ylboronic acid (0.90 g, 4.35 mmol, Aldrich, St. Louis, Mo.) and tetrakis(triphenylphosphine)palladium(0) (0.13 g, 0.11 mmol, Strem Chemicals, Inc., Newburyport, Mass.) in dioxane (3 mL) and water (1 mL) was sealed and purged with argon for several minutes. The reaction mixture was stirred at 90° C. for 6 h and then allowed to cool to room temperature. The organic phase was taken and the solvents removed under vacuum. Purification of the crude reaction mixture by silica gel chromatography (0 to 3% MeOH/CH2Cl2) provided the title compound as an orange solid. m/z (ESI, +ve ion) 380 (M+H)+.

Workup

customwas sealed
custompurged with argon for several minutes
temperatureto cool to room temperature
customthe solvents removed under vacuum
customPurification of the crude
customreaction mixture by silica gel chromatography (0 to 3% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-e6bf2c1d28ed41ac871beb8d9c2a5375
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362241B2

Reaction notes

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