Benzophenone imine → HCID 57494447、化合物

HRID 2262626ノート

反応式

HRID 2262626 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 57494447HCID 57494447、化合物

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0d25781243084631839536871f204790
出典データセット
uspto-grants-2010_12
特許番号
US07851463B2

反応ノート

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