1,2-Dimethoxyethane → HCID 178420863, compound

HRID 1811848Notes

Reaction equation

HRID 1811848 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]2C1CCCCO1.Br[C:19]1[CH:20]=[C:21](B(O)O)C(F)=N[CH:24]=1.C(=O)([O-])[O-:30].[K+].[K+].COCCOC>ClCCl.[Pd+2].[Cl-].[Cl-].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[O:30]1[CH2:24][CH2:19][CH2:20][CH2:21][CH:11]1[C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][NH:6]2)=[CH:2][N:10]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27832425-Bromo-2-fluoropyridine-3-boronic Acid (contains varying amounts of Anhydride)HCID 595482686-chloro-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Product 1

HCID 178420863HCID 178420863, compound

Reagents, catalysts & solvents 2

HCID 178478474HCID 178478474, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A glass microwave reaction vessel was charged with 6-chloro-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (0.525 g, 2 mmol), 5-bromo-2-fluoropyridine-3-boronic acid (0.5 g, 2 mmol) (Alfa Aesar, Ward Hill, Mass.), potassium carbonate (0.5 g, 9 mmol), (Aldrich, St. Louis, Mo.) dichloro[1,1′-bis(diphenylphosphino)ferrocene]dichloride palladium(II) dichloromethane adduct (0.2 g, 0.2 mmol) (Strem Chemicals, Inc., Newburyport, Mass.). A deoxygenated mixture of 1,2-dimethoxyethane (10 mL, 96 mmol) (Aldrich, St. Louis, Mo.) and water (1 mL) was added. The vial was deoxygenated for 5 minutes, capped, and the reaction mixture was stirred at 100° C. for 2 h. The crude product was adsorbed onto a plug of silica gel and chromatographed through a RediSep®, Teledyne ISCO, Lincoln, Nebr., pre-packed silica gel column (120 g), eluting with a gradient of 20% to 80% ethyl acetate in hexane to provide 6-(5-bromo-2-fluoropyridin-3-yl)-2-methyl-9-(tetrahydro-2-H-pyran-2-yl-9H-purine. m/z (ESI, +ve) 392/394 (M+H)+.

Workup

  1. customA glass microwave reaction vessel
  2. additionwas added
  3. customThe vial was deoxygenated for 5 minutes
  4. customcapped
  5. customchromatographed through a RediSep®, Teledyne ISCO, Lincoln, Nebr
  6. wash, pre-packed silica gel column (120 g), eluting with a gradient of 20% to 80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-83131bc735a2410796647f494960f7e7
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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