HCID 178483072, compound → HCID 178483071, compound

HRID 1984915Notes

Reaction equation

HRID 1984915 reaction equation
C(OC(=O)[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][NH:18][C:19]2[N:28]=[C:27]([N:29]([CH3:31])[CH3:30])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1>CO.[Pd]>[NH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][NH:18][C:19]2[N:28]=[C:27]([N:29]([CH3:31])[CH3:30])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 178483072HCID 178483072, compound

Product 1

HCID 178483071HCID 178483071, compoundYield 109.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of trans-{4-[(4-dimethylamino-quinazolin-2-ylamino)-methyl]-cyclohexyl}-carbamic acid benzyl ester obtained in step C of example 3 (330 mg, 0.76 mmol) in MeOH (3.3 mL) was added 10% Pd/C (33 mg). The mixture was stirred at ambient temperature under hydrogen atmosphere for 25 hr, filtered, concentrated, and purified by flash chromatography (NH-silica gel, 50% EtOAc in hexane) to give trans-N2-(4-amino-cyclohexylmethyl)-N4,N4-dimethyl-quinazoline-2,4-diamine (250 mg, 98%) as a pale yellow oil.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. custompurified by flash chromatography (NH-silica gel, 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-9a6df690db2f46748152f0ea7d463c03
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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