Benzophenone imine → HCID 57494447, compound

HRID 2262626Notes

Reaction equation

HRID 2262626 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([CH:8]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH3:15])[CH2:9]2)=[N:6][CH:7]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+].C(=[NH:81])(C1C=CC=CC=1)C1C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH2:13]([N:10]1[CH2:11][CH2:12][CH:8]([C:5]2[N:4]=[CH:3][C:2]([NH2:81])=[CH:7][N:6]=2)[CH2:9]1)[CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 57470082Pyrimidine, 5-bromo-2-(1-propyl-3-pyrrolidinyl)-

Product 1

HCID 57494447HCID 57494447, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A dry flask was charged with 5-bromo-2-(1-propyl-pyrrolidin-3-yl)-pyrimidine (300 mg, 1.11 mmol), Pd2(dba)3 (tris(dibenzylideneacetonate) dipalladium (30 mg, 0.032 mmol)), rac-BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) (35 mg, 0.056 mmol), tBuONa (150 mg, 1.56 mmol), benzophenone imine (300 mg, 1.65 mmol) and toluene (4 ml). It was then evacuated, flushed with nitrogen and the mixture heated at 80° C. under microwave irradiations for 3 h. After filtration through a pad of celite, the solvent was removed under reduced pressure. The crude material was then dissolved in THF (10 ml) and 1 N aqueous HCl (3 ml) was added. The solution was stirred at room temperature for 45 min and the organic solvent was next removed under vacuo. The resulting aqueous phase was adjusted to pH˜9 with 2 N NaOH solution, washed with heptane:ethyl acetate, 2:1 (50 ml) and concentrated to give the crude amine.

Workup

  1. customIt was then evacuated
  2. customflushed with nitrogen
  3. filtrationAfter filtration through a pad of celite
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe crude material was then dissolved in THF (10 ml)
  6. addition1 N aqueous HCl (3 ml) was added
  7. customthe organic solvent was next removed under vacuo
  8. washwashed with heptane
  9. concentrationethyl acetate, 2:1 (50 ml) and concentrated

Sources & evidence

ORD record
ord-0d25781243084631839536871f204790
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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