Triethylamine → Quinazoline

HRID 325285Notes

Reaction equation

HRID 325285 reaction equation
N[C:2]1[C:11]2[C:6](=[CH:7][C:8](OC)=[C:9](OC)[CH:10]=2)[N:5]=[C:4](N2CCNCC2)[N:3]=1.C(N(CC)CC)C>C(COC)OC>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

Product 1

HCID 9210Quinazoline

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

In accordance with the foregoing reaction scheme, a 4-nitrophenylalkanoic acid (1) is reacted with phosphorous trichloride, such as by heating at reflux in a suitable solvent, to obtain the corresponding acid chloride (2). The latter is reacted with 4-amino-6,7-dimethoxy-2-(1-piperazinyl) quinazoline (3) and triethyl amine (TEA) in dimethoxy ethane (DME) to obtain the 4-amino-6,7-dimethoxy-2-[4-[4-nitrophenyl]-alkanoyl)-1-piperazinyl] quinazoline intermediate (4). The 4-nitrophenyl intermediate (4) is then subjected to catalytic hydrogenation, such as in the presence of a palladium-on-carbon (Pd/C) catalyst, to obtain the desired 4-aminophenyl product (5).

Sources & evidence

ORD record
ord-ffb2293747024d84a36bd7aafe657e2d
Source dataset
uspto-grants-1984_04
Patent number
US04440769

Reaction notes

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