Quinazoline → 2,4-Diamino-5-chloro-6-(5-chloro-2-hydroxyphenyl)quinazoline

HRID 52618

Reaction equation

HRID 52618 reaction equation
N1C2C(=CC=CC=2)C=NC=1.[NH2:11][C:12]1[N:21]=[C:20]([NH2:22])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=3[O:31]C)[C:18]=2[Cl:23])[N:13]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:11][C:12]1[N:21]=[C:20]([NH2:22])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=3[OH:31])[C:18]=2[Cl:23])[N:13]=1

Participants

5

Reactant 3

HCID 9210QuinazolineHCID 25134Boron tribromideHCID 540726682,4-Diamino-5-chloro-6-(5-chloro-2-methoxyphenyl)quinazoline2×

Product 1

HCID 543690952,4-Diamino-5-chloro-6-(5-chloro-2-hydroxyphenyl)quinazoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A series of quinazoline analogs may be prepared from the above 2,4-diamino-5-chloro-6-(5-chloro-2-methoxyphenyl)quinazoline. This is accomplished by the reaction of 2,4-diamino-5-chloro-6-(5-chloro-2-methoxyphenyl)quinazoline with 1M boron tribromide in methylene chloride, yielding the corresponding 2,4-diamino-5-chloro-6-(5-chloro-2-hydroxyphenyl)quinazoline. The hydroxy intermediate in turn is reacted with a halogen-containing compound and potassium carbonate in N,N-dimethylformamide, affording the appropriately 6-(5-chloro-2-substituted-phenyl)quinazoline, for example, 2,4-diamino-5-chloro-6-[5-chloro-2-(pyridin-2-ylmethoxy)phenyl]quinazoline. Example 3 describes in detail the preparation of this compound.

Sources & evidence

ORD record
ord-7bbc177f69574626b20c30222e1109fd
Source dataset
uspto-grants-1997_04
Patent number
US05616718

Linked notes

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