1,4-Cyclohexadiene → HCID 178483076, compound

HRID 1984935Notes

Reaction equation

HRID 1984935 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][C@H:13]1[CH2:18][CH2:17][C@@H:16]([NH:19][C:20]2[N:29]=[C:28]([N:30]([CH3:32])[CH3:31])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)[CH2:15][CH2:14]1)C1C=CC=CC=1.C1CC=CCC=1>CCO.[Pd]>[NH2:10][CH2:11][CH2:12][C@@H:13]1[CH2:14][CH2:15][C@H:16]([NH:19][C:20]2[N:29]=[C:28]([N:30]([CH3:31])[CH3:32])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)[CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 178483077HCID 178483077, compound

Product 1

HCID 178483076HCID 178483076, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of cis-{2-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexyl]-ethyl}-carbamic acid benzyl ester (4.47 g, 10 mmol) in EtOH (20 mL) was added 1,4-cyclohexadiene (20 mL) and 200 mg of 10% Pd/C. The reaction mixture was stirred at ambient temperature for 18 hr, filtered through pad of celite, and concentrated. The residue was purified by column chromatography (silica gel, 5% to 15% 2 M NH3/MeOH in CH2Cl2) to give cis-N2-[4-(2-amino-ethyl)-cyclohexyl]-N4,N4-dimethyl-quinazoline-2,4-diamine (2.41 g, 77%) as a yellow oil.

Workup

  1. filtrationfiltered through pad of celite
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography (silica gel, 5% to 15% 2 M NH3/MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-35acf229bc23468291691d526e1bac64
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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