Hydrochloric Acid → N-[5-(7-Benzyloxy-6-methoxy-quinazolin-4-ylamino)-pyrimidin-2-yl]-benzamide Dihydrochloride

HRID 1686007Notes

Reaction equation

HRID 1686007 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:19])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][C:23]1[CH:24]=[N:25][C:26]([NH:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:27][CH:28]=1.[ClH:38].O1CCOCC1>CC(N(C)C)=O>[ClH:19].[ClH:38].[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:22][C:23]3[CH:24]=[N:25][C:26]([NH:29][C:30](=[O:37])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[N:27][CH:28]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazolineHCID 11499482N-(5-aminopyrimidin-2-yl)benzamide

Product 1

HCID 67264803N-[5-(7-Benzyloxy-6-methoxy-quinazolin-4-ylamino)-pyrimidin-2-yl]-benzamide Dihydrochloride

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 7-benzyloxy-4-chloro-6-methoxy-quinazoline (760 mg, 2.53 mmol) and N-(5-amino-pyrimidin-2-yl)-benzamide (542 mg, 2.53 mmol) in DMA was added 4N HCl in dioxane (822 μl, 3.29 mmol) and the reaction heated at 50° C. for 4 hours under nitrogen. The reaction was cooled and filtered. The precipitate was washed with Et2O and dried under reduced pressure to provide the title compound as a light tan brown solid (706 mg).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. washThe precipitate was washed with Et2O
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-99c1b23da4e64149ada4bee4a166c6fd
Source dataset
uspto-grants-2012_04
Patent number
US08148531B2

Reaction notes

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