Sodium Carbonate → 4-Chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine

HRID 28569

Reaction equation

HRID 28569 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH2:21][CH3:22])=[C:15](B(O)O)[CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(C)=O.C(COC)OC>[Cl:8][C:6]1[CH:7]=[C:2]([C:13]2[CH:12]=[C:11]([Cl:10])[CH:16]=[CH:15][C:14]=2[O:20][CH2:21][CH3:22])[N:3]=[C:4]([NH2:9])[N:5]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 655222-Amino-4,6-dichloropyrimidineHCID 37008365-Chloro-2-ethoxyphenylboronic acid

Product 1

HCID 860043254-Chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamineYield 73.3%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 4,6-dichloro-pyrimidin-2-ylamine (0.50 g, 3.0 mmol), 5-chloro-2-ethoxy-phenyl boronic acid (0.61 g, 3.0 mmol), palladium (II) acetate (0.10 g, 0.46 mmol), and triphenylphosphine (0.24 g, 0.91 mmol) was added a solution of sodium carbonate (1.6 g, 15.2 mmol) in water (5 ml) followed by glyme (20 ml). The mixture was stirred under an argon atmosphere at room temperature for 3.5 hours. Acetone (20 ml) was added and the mixture was filtered through a pad of celite under suction. The filtrated was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with 15% ethyl acetate-hexane followed by 20% ethyl acetate-hexane to provide 4-chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine (0.625 g, 73% yield) as a white powder.

Workup

  1. filtrationthe mixture was filtered through a pad of celite under suction
  2. concentrationThe filtrated was concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography on silica gel eluting with 15% ethyl acetate-hexane

Sources & evidence

ORD record
ord-582a73f2ba0f47c68b8c414e243374b1
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

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