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ChemicalBook CAS DataBase List 4-Chloro-6,7-dimethoxyquinazoline
13790-39-1

4-Chloro-6,7-dimethoxyquinazoline synthesis

13synthesis methods
-

Yield:13790-39-1 98%

Reaction Conditions:

with thionyl chloride in N,N-dimethyl-formamide for 6 h;Heating / reflux;

Steps:

1.b Example 1
b) Dimethylformamide (0.2 ml) was added dropwise to a solution of 6,7-dimethoxy-3,4-dihydro-quinazolin-4-one (10.0 g, 48.5 mmol) in thionyl chloride (200ml) and the reaction was heated at reflux for 6 hours. The reaction was cooled, excess thionyl chloride was removed in vacuo and the residue was azeotroped with toluene (2 x 50 ml) to remove the last of the thionyl chloride. The residue was taken up in dichloromethane (550 ml), the solution was washed with i) saturated aqueous sodium hydrogen carbonate solution (2 x 250 ml) and ii) brine, and the organic phase was dried over magnesium sulphate. Solvent evaporation in vacuo yielded 4-chloro-6,7-dimethoxyquinazoline (10.7 g, 98 % yield) as a white solid: 1H-NMR (DMSO d6): 8.86 (s, 1H), 7.42 (s, 1H), 7.37 (s, 1H), 4.00 (s, 3H), 3.98 (s, 3H): MS (+ve ESI): 225 (M-H)+.

References:

AstraZeneca AB EP1218357, 2005, B1 Location in patent:Page/Page column 14

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