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Sodium Carbonate → 6-(2-Ethoxyphenyl)pyrimidin-4-amine

HRID 1020026
Notes
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Reaction equation

HRID 1020026 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B(O)O)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[NH2:19][C:20]1[CH:25]=[C:24](Cl)[N:23]=[CH:22][N:21]=1>O1CCOCC1.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>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:24]1[N:23]=[CH:22][N:21]=[C:20]([NH2:19])[CH:25]=1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2380124-Amino-6-chloropyrimidineHCID 2734902(2-Ethoxyphenyl)boronic acid

Product 1

HCID 595089836-(2-Ethoxyphenyl)pyrimidin-4-amineYield 96.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 31275
1,4-Dioxane
Solvent

Procedure

To a solution of 2-ethoxyphenylboronic acid (II) (1.73 g, 10.4 mmol) in 30 ml of 1,4-dioxane 10 ml of saturated aqueous sodium carbonate solution were added. Argon gas was purged for 10 min at room temperature. 6-Chloro-pyrimidin-4-ylamine (I) (1.50 g, 11.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.66 g, 0.57 mmol) were added to the reaction mixture simultaneously and argon gas was bubbled in for another 5 min. The reaction mixture was heated to reflux for 12 hours. After completion of the reaction as indicated by TLC the mixture was concentrated under reduced pressure. The residue was partitioned between dichloromethane and water. The organic layer was separated, washed with water and brine, dried over sodium sulfate and concentrated. The obtained crude residue was purified by column chromatography eluting with 15% ethyl acetate in dichloromethane to provide 6-(2-ethoxy-phenyl)-pyrimidin-4-ylamine (III) (2.17 g, 87.3%).

Workup

  1. customArgon gas was purged for 10 min at room temperature
  2. customargon gas was bubbled in for another 5 min
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 12 hours
  5. customAfter completion of the reaction
  6. concentrationwas concentrated under reduced pressure
  7. customThe residue was partitioned between dichloromethane and water
  8. customThe organic layer was separated
  9. washwashed with water and brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated
  12. customThe obtained crude residue
  13. customwas purified by column chromatography
  14. washeluting with 15% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-1de56c094ee240d29b338da8ce79b6b0
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08716296B2

Reaction notes

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