Potassium Carbonate → 4-[3-(4-amino-[1,3,5]triazin-2-yl)-2-methyl-3H-benzoimidazol-5-yl]-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-but-3-yn-2-ol

HRID 1398707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398707
[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][CH2:7][C:8]([CH3:12])([OH:11])[C:9]#[CH:10])([CH3:4])([CH3:3])[CH3:2].Br[C:16]1[CH:17]=[CH:18][C:19]2[N:23]=[C:22]([CH3:24])[N:21]([C:25]3[N:30]=[CH:29][N:28]=[C:27]([NH2:31])[N:26]=3)[C:20]=2[CH:32]=1.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].[Cu]I>[NH2:31][C:27]1[N:28]=[CH:29][N:30]=[C:25]([N:21]2[C:20]3[CH:32]=[C:16]([C:10]#[C:9][C:8]([CH3:12])([OH:11])[CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:14])[CH3:13])[CH:17]=[CH:18][C:19]=3[N:23]=[C:22]2[CH3:24])[N:26]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 110959763-Butyn-2-ol, 1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-2×HCID 681818904-(6-Bromo-2-methyl-benzoimidazol-1-yl)-[1,3,5]triazin-2-ylamine

Produkt 1

HCID 681817704-[3-(4-amino-[1,3,5]triazin-2-yl)-2-methyl-3H-benzoimidazol-5-yl]-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-but-3-yn-2-olAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

The title compound was prepared by procedure described in Example 144, by substituting 2-ethynylbicyclo [2.2.1]heptan-2-ol with 1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-but-3-yn-2-ol. A mixture of 4-(6-bromo-2-methyl-benzoimidazol-1-yl)-[1,3,5]triazin-2-ylamine (300 mg, 0.98 mmol), 1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-but-3-yn-2-ol (380 mg, 1.9 mmol) in DMF (2.5 mL) was treated with Pd(OAc)2 (20 mg, 0.1 mmol), dppp (60 mg, 0.2 mmol), CuI (5 mg, 0.05 mmol) and K2CO3 (280 mg, 2.0 mmol), then the mixture was heated at 120° C. for 40 min under microwave. After filtrated and concentrated by vacuum, the residue was purified by silica gel chromatography (DCM: MeOH=20:1) to get the title compound 4-[3-(4-amino-[1,3,5]triazin-2-yl)-2-methyl-3H-benzoimidazol-5-yl]-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-but-3-yn-2-ol (7-b) (300 mg, yield 68%).

Aufarbeitung

  1. customThe title compound was prepared by procedure
  2. filtrationAfter filtrated
  3. concentrationconcentrated by vacuum
  4. customthe residue was purified by silica gel chromatography (DCM: MeOH=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-e1e7c712b5de4b66b6ed042c7a63e6b9
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901313B2

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