Sodium Carbonate → HCID 66990684, compound

HRID 454470Notes

Reaction equation

HRID 454470 reaction equation
Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:14]([O:21][C:22]1[CH:37]=[CH:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][C:23]=1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.O.COCCOC>[CH2:14]([O:21][C:22]1[CH:37]=[CH:36][C:35]([C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:34][C:23]=1[C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 783452-BromopyrimidineHCID 66990200HCID 66990200, compound

Product 1

HCID 66990684HCID 66990684, compoundYield 87.2%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Water (5.3 mL), 2-bromopyrimidine (0.95 g), sodium carbonate (1.3 g), and bis(triphenylphosphine)palladium(II) dichloride (0.14 g) were added to an ethylene glycol dimethyl ether (18 mL) solution of the obtained benzyl 2-(benzyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1.8 g), followed by heating to reflux under a nitrogen atmosphere for 4 hours. The reaction mixture was cooled to room temperature, an then bis(triphenylphosphine)palladium(II) dichloride (0.14 g) was added thereto, followed by heating to reflux under a nitrogen atmosphere for 5 hours. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 80-50% hexane/ethyl acetate] to obtain 1.4 g of benzyl 2-(benzyloxy)-5-(pyrimidin-2-yl)benzoate.

Workup

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 4 hours
  3. temperatureby heating
  4. temperatureto reflux under a nitrogen atmosphere for 5 hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography [eluent: 80-50% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-5d9888abb17f4583b882964725e87d88
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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