Sodium Azide → 4-Quinazolinamine, 2-azido-N-(4-methoxyphenyl)-N-methyl-

HRID 1436295Notes

Reaction equation

Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+]>>[N:22]([C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)=[N+:23]=[N-:24]

Participants

Reactant 2

HCID 33557Sodium Azide

HCID 117381122-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine

Product 1

HCID 114040004-Quinazolinamine, 2-azido-N-(4-methoxyphenyl)-N-methyl-

Procedure

The title compound was prepared from (2-chloro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine (150 mg, 0.5 mmol), sodium azide (97.5 mg, 1.5 mmol) in 5 mL of solvent (THF:MeOH:water=0.3:1:1) by a procedure similar to that of example 120 (4%). 1H NMR (CDCl3): 8.45 (d, J=8.4 Hz, 1H), 7.78-7.72 (m, 1H), 7.27-7.22 (m, 2H), 7.19-7.14 (m, 2H), 6.95 (d, J=8.7 Hz, 2H), 3.86 (s, 3H), 3.69 (s, 3H).

Sources & evidence

ORD record: ord-4ab0c0aaa4c64090bf6aced1737f031e
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618975B2

Reaction notes

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