Hydrochloric Acid → HCID 178483061, compound

HRID 1984884Notes

Reaction equation

HRID 1984884 reaction equation
C(OC(=O)[NH:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][NH:16][C:17]2[N:26]=[C:25]([N:27]([CH3:29])[CH3:28])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:11][CH2:10]1)(C)(C)C.Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[NH2:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][NH:16][C:17]2[N:26]=[C:25]([N:27]([CH3:29])[CH3:28])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178483065HCID 178483065, compound

Product 1

HCID 178483061HCID 178483061, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of trans-{4-[(4-dimethylamino-quinazolin-2-ylamino)-methyl]-cyclohexylmethyl}-carbamic acid tert-butyl ester (20.1 g, 48.6 mmol) in EtOAc (200 mL) was added 4 M hydrogen chloride in EtOAc (200 mL). The mixture was stirred at ambient temperature for 90 min and concentrated to give a solid. The solid was alkalized with saturated aqueous NaHCO3 (pH=9), concentrated, and purified by flash chromatography (NH silica gel, 33% MeOH in CHCl3) to give trans-N2-(4-aminomethyl-cyclohexylmethyl)-N4,N4-dimethyl-quinazoline-2,4-diamine (14.7 g, 97%) as a white solid.

Workup

  1. concentrationconcentrated
  2. customto give a solid
  3. concentrationconcentrated
  4. custompurified by flash chromatography (NH silica gel, 33% MeOH in CHCl3)

Sources & evidence

ORD record
ord-f03f944700414d50b99886d6e7ce9bca
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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