4-Chloro-6,7-dimethoxyquinazoline → (6,7-Dimethoxyquinazolin-4-yl)-(3-ethynylphenyl)-amine Hydrochloride

HRID 1869079Notes

Reaction equation

HRID 1869079 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C[Si](C)(C)[C:18]#[C:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1F)[NH2:23]>C(O)(C)(C)C>[ClH:1].[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][N:3]=[C:2]2[NH:23][C:22]1[CH:24]=[CH:25][CH:26]=[C:20]([C:19]#[CH:18])[CH:21]=1

Participants

4

Reactant 2

HCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 126873584-Fluoro-3-((trimethylsilyl)ethynyl)aniline

Product 1

HCID 18925020(6,7-Dimethoxyquinazolin-4-yl)-(3-ethynylphenyl)-amine Hydrochloride

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

4-Chloro-6,7-dimethoxyquinazoline (500 mg, 2.23 mmol) and 3-(2′-trimethylsilylethynyl)-4-fluoroaniline (507 mg, 2.44 mmol) were refluxed in 5 mL of tert-butyl alcohol for 16 hours, cooled and filtered to afford solid (6,7-dimethoxy-quinazolin-4-yl)-(3′-ethynyl-phenyl)-amine hydrochloride which was washed with 10 mL of isopropyl alcohol and dried in vacuo at 70° C., 832 mg (83%). This was reacted in 10 mL of methanol and 1 drop of water containing 250 mg of potassium carbonate for 3 hours. The mixture was filtered and the filtrate vacuum evaoprated. This residue was triturated for 1 hour with 1N hydrochloric acid, filtered and washed with a minimum amount of water then methanol and dried in vacuo; 506 mg (63%) mp 229° C. dec.

Workup

  1. temperaturecooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-a030c43e234f497a8be5952c9adee158
Source dataset
uspto-grants-2009_12
Patent number
USRE041065E1

Reaction notes

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