Sodium Carbonate → HCID 4188102, compound

HRID 1835465Notes

Reaction equation

HRID 1835465 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>[Pd]>[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 783445-BromopyrimidineHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 4188102HCID 4188102, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of 5-bromopyrimidine(1.52 g),2-methylphenylboronic acid (1.43 g), sodium carbonate (3.04 g) and 10% palladium on charcoal (50% wet, 0.85 g) was refluxed for 24 hours. The mixture was filtered and the filtrate was concentrated under reduced pressure. To the residue ethyl acetate was added and the mixture was washed with water and brine. The separated organic layer was dried over magnesium sulfate and evaporated under pressure to give 5-(2-methylphenyl)pyrimidine (1.61 g, 98.7%).

Workup

  1. temperaturewas refluxed for 24 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the residue ethyl acetate was added
  5. washthe mixture was washed with water and brine
  6. dry with materialThe separated organic layer was dried over magnesium sulfate
  7. customevaporated under pressure

Sources & evidence

ORD record
ord-bc92d2d36cfa45b088fab5a26407fa89
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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