HCID 178483079, compound → HCID 68846891, compound

HRID 1984908Notes

Reaction equation

HRID 1984908 reaction equation
C(OC(=O)[NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([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)[CH2:14][CH2:13]1)C1C=CC=CC=1>CO.[Pd]>[NH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][CH:15]([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)[CH2:16][CH2:17]1

Participants

4

Reactant 1

HCID 178483079HCID 178483079, compound

Product 1

HCID 68846891HCID 68846891, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of cis-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexylmethyl]-carbamic acid benzyl ester obtained in step B of example 24 (12.1 g, 27.9 mmol) in MeOH (120 mL) was added 10% Pd/C (1.21 g). The mixture was stirred at 50° C. under hydrogen atmosphere for 19 hr, filtered, concentrated, and purified by flash chromatography (NH-silica gel, 66% EtOAc in hexane to 15% MeOH in chloroform) to give N2-(4-aminomethyl-cyclohexyl)-N4,N4-dimethyl-quinazoline-2,4-diamine (6.9 g, 83%) as a yellow solid.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. custompurified by flash chromatography (NH-silica gel, 66% EtOAc in hexane to 15% MeOH in chloroform)

Sources & evidence

ORD record
ord-b5bf2f57bbea4696ae2ee0eefeee1f75
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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