4-Chloro-6-methoxyquinazolin-7-ol → 4-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline

HRID 1690484Notes

Reaction equation

HRID 1690484 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1>COCCO>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:8][CH2:9][O:12][CH3:13])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 1357422514-Chloro-6-methoxyquinazolin-7-ol

Product 1

HCID 107306534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazolineYield 100%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

Using analogous procedures to those described in the portion of Note [1] above that is concerned with the preparation of starting materials, 4-chloro-7-hydroxy-6-methoxyquinazoline was reacted with 2-methoxyethanol to give 4-chloro-6-methoxy-7-(2-methoxyethoxy) quinazoline in 100% yield; 1H NMR: (CDCl3) 3.49 (s, 3H), 3.89 (t, 2H), 4.05 (s, 3H), 4.35 (t, 2H), 7.26 (s, 1H), 7.35 (s, 1H), 8.86 (s, 1H); Mass Spectrum: M+H+ 269; which in turn was reacted with 2-(4-hydroxyphenyl)acetic acid to give the required starting material in 99% yield; 1H NMR: (DMSOd6) 3.35 (s, 3H), 3.63 (s, 2H), 3.76 (m, 2H), 3.98 (s, 3H), 4.33 (m, 2H), 7.25 (d, 2H), 7.36 (d, 2H), 7.4 (s, 1H), 7.56 (s, 1H), 8.54 (s, 1H); Mass Spectrum: M+H+ 385.

Sources & evidence

ORD record
ord-11227045a6b1480ab5bc2796e0be431a
Source dataset
uspto-grants-2012_04
Patent number
US08153643B2

Reaction notes

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