Sodium Carbonate → 4,6-diphenylpyrimidin-2-amine

HRID 1513624Notes

Reaction equation

HRID 1513624 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4](Cl)[N:3]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 655222-Amino-4,6-dichloropyrimidineHCID 66827Phenylboronic Acid

Product 1

HCID 6190244,6-diphenylpyrimidin-2-amineYield 77%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Amino-4,6-dichloropyrimidine 9.5 g (58 mmol), phenylboronic acid 17 g (140 mmol) and tetrakis(triphenylphosphine)palladium 2.7 g (2.3 mmol) were dissolved in 120 mL of 1,2-dimethoxyethane. A 2.0M sodium carbonate aqueous solution 60 mL was added thereto, and the solution was refluxed for 8 hours under argon atmosphere by heating. After finishing the reaction, the aqueous layer was removed. The organic layer was dried on anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was refined by silica gel chromatography to obtain 11 g (yield: 77%) of 2-amino-4,6-diphenylpyrimidine.

Workup

  1. temperaturethe solution was refluxed for 8 hours under argon atmosphere
  2. temperatureby heating
  3. customthe reaction
  4. customthe aqueous layer was removed
  5. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1ce274994f0249ca9e9e900ffc054674
Source dataset
uspto-grants-2012_07
Patent number
US08217570B2

Reaction notes

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