1-Butanol → HCID 44479178, compound

HRID 1880029Notes

Reaction equation

HRID 1880029 reaction equation
Br[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)CCC>CCOC(C)=O.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

7

Reactant 4

HCID 2631-ButanolHCID 517044Potassium AcetateHCID 27832702-Fluoropyridine-3-boronic acidHCID 583686166-Bromo-9-(tetrahydro-2H-pyran-2-YL)-9H-purine

Product 1

HCID 44479178HCID 44479178, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask, under a reflux condenser, was added 6-bromo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (1.0 g, 3.5 mmol), 2-fluoropyridin-3-ylboronic acid (0.75 g, 5.3 mmol), potassium acetate (1.0 g, 11 mmol), 1-butanol (50 mL) and DI water (10 mL). The mixture was purged with Ar (vacuum/purge three times) to remove oxygen, then PdCl2(P-tert-Bu2Ph)2 (0.026 g, 0.042 mmol) was added. The reaction mixture was stirred in a 100° C. oil bath for 45 min (complete by TLC, 80% EtOAc/hex).

Workup

  1. customThe mixture was purged with Ar (vacuum/purge three times)
  2. customto remove oxygen

Sources & evidence

ORD record
ord-2e464a9a63f7475595a8900afacbc282
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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