4-Chloroquinazoline → 4-Aminoquinazoline

HRID 2369810Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.CC[N:14](C(C)C)C(C)C>>[NH2:14][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

Reactant 2

HCID 788644-Chloroquinazoline

HCID 81531Diisopropylethylamine

Product 1

HCID 847594-Aminoquinazoline

Procedure

4-Chloro quinazoline derivative 3a was reacted with the primary amine 2d in the presence of Hunig's base to provide the 4-amino quinazoline intermediate 3b. Ammonolysis of the ester group with 7N ammonia/methanol solution afforded carboxamide 3c. When R4 is a protecting Nosyl group, deprotection with cesium carbonate in the presence of thiophenol provides 3d.

Sources & evidence

ORD record: ord-bcd89f69e8dd48938b91cb9e5cf76923
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710044B2

Reaction notes

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