Sodium Carbonate → HCID 67280484, compound

HRID 1694694Notes

Reaction equation

HRID 1694694 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1B(O)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:20]1[CH:21]=[N:22][CH:23]=[N:24][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:20]1[CH:21]=[N:22][CH:23]=[N:24][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 783445-BromopyrimidineHCID 41987402-Benzyloxy-5-chlorobenzeneboronic acid

Product 1

HCID 67280484HCID 67280484, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product from step (ii) (0.2 g), 5-bromopyrimidine (0.16 g), sodium carbonate (0.21 g) and tetrakistriphenylphosphine palladium (0) (0.05 g) in dioxane (6 ml) was heated under reflux for 48 h. The mixture was partitioned between EtOAc and water, the organics separated, dried, and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 20% EtOAc/isohexane. Yield 0.283 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 h
  3. customThe mixture was partitioned between EtOAc and water
  4. customthe organics separated, dried
  5. customevaporated under reduced pressure
  6. customThe residue was purified by chromatography on silica eluting with 20% EtOAc/isohexane

Sources & evidence

ORD record
ord-56c76e081bfa4de4aff846e489a5f156
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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