Water → HCID 57970143, compound

HRID 1666606Notes

Reaction equation

HRID 1666606 reaction equation
[CH:1]1([Mg]Br)C[CH2:5][CH2:4][CH2:3][CH2:2]1.C[N:10]1CCCC1.[Cl:15][C:16]1[CH:25]=[C:24](Cl)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.O>C(OCC)C.C1COCC1.[Cl-].[Zn+2].[Cl-].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Cl:15][C:16]1[N:10]=[C:24]([CH:25]2[CH2:5][CH2:4][CH2:3][CH2:2][CH2:1]2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1

Participants

9

Reactant 4

HCID 962WaterHCID 84541-MethylpyrrolidineHCID 6075032,4-DichloroquinolineHCID 178419651HCID 178419651, compound

Product 1

HCID 57970143HCID 57970143, compound

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2 M cyclohexylmagnesium bromide in diethyl ether (3.3 mL) was added a solution of 0.5 M zinc chloride in THF (14 mL) under nitrogen atmosphere, and the mixture was stirred at room temperature for 20 min. N-methylpyrrolidine (10 mL) was added, the mixture was stirred for 5 min, followed by addition of Pd(PtBu3)2 (0.13 g) and 2,4-dichloroquinoline (1.0 g), and the mixture was stirred at room temperature for 4 h. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate, the desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=6:1) to obtain 2-chloro-4-cyclohexylquinazoline (1.1 g).

Workup

  1. stirringthe mixture was stirred for 5 min
  2. stirringthe mixture was stirred at room temperature for 4 h
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. customthe desiccant was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=6:1)

Sources & evidence

ORD record
ord-1c428a70d35e4870911a3d99916109de
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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