Benzophenone imine → HCID 57494447, 화합물

HRID 2262626노트

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HRID 2262626 반응식
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]

참가 물질

7

반응물 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 574700825-Bromo-2-(1-propylpyrrolidin-3-yl)pyrimidine

생성물 1

HCID 57494447HCID 57494447, 화합물

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0d25781243084631839536871f204790
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851463B2

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