2,4-Diamino-5-chloro-6-nitroquinazoline → 2,4,6-Triaminoquinazoline

HRID 52615Notes

Reaction equation

HRID 52615 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:14]([O-])=O)[C:8]=2Cl)[N:3]=1>[Pd]>[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:14])[CH:8]=2)[N:3]=1

Participants

3

Reactant 1

HCID 125168262,4-Diamino-5-chloro-6-nitroquinazoline

Product 1

HCID 2926612,4,6-Triaminoquinazoline

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a similar manner 2,4,6-triaminoquinazoline and 2,4,6-triamino-5-chloroquinazoline can be prepared. This is accomplished by the nitration of, for example, 2,4-diamino-5-chloroquinazoline (above) with 90% nitric acid and sulfuric acid, yielding the corresponding 2,4-diamino-5-chloro-6-nitroquinazoline. The 6-nitroquinazoline is in turn reduced by either hydrogenation in the presence of 10% palladium on carbon or by treatment with stannous chloride dihydrate, affording the corresponding 2,4,6-triaminoquinazoline. Steps A and B of Example 15 describe in detail these two steps in the reaction sequence.

Sources & evidence

ORD record
ord-764df47bfc5a4bf1a229c0cbf3ff4f41
Source dataset
uspto-grants-1997_04
Patent number
US05616718

Reaction notes

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