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ChemicalBook CAS DataBase List 6-BROMO-2-QUINAZOLINAMINE
190273-89-3

6-BROMO-2-QUINAZOLINAMINE synthesis

6synthesis methods
Guanidine carbonate

593-85-1

5-Bromo-2-fluorobenzaldehyde

93777-26-5

6-BROMO-2-QUINAZOLINAMINE

190273-89-3

5-Bromo-2-fluorobenzaldehyde (10 g, 49.2 mmol) and guanidine carbonate (13.3 g, 74 mmol) were dissolved in N,N-dimethylacetamide (50 mL). The reaction mixture was heated to reflux temperature with continuous stirring for 5 hours. Upon completion of the reaction, it was cooled to room temperature, water (120 mL) was added and stirring was continued for 2 hours at room temperature. The resulting 6-bromo-2-quinazolinamine was collected by filtration and subsequently dried under vacuum to give the final product (5.0 g, 60% yield).

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Yield:190273-89-3 73%

Reaction Conditions:

in N,N-dimethyl acetamide at 150; for 5 h;

Steps:

6-Bromoquinazolin-2-amine (3).32

Guanidine carbonate (2) (4.47 g, 36.9 mmol) was added to a solution of 5-bromo-2-fluorobenzaldehyde (1) (5.00 g, 24.6 mmol) in dimethylacetamide (50 ml). The reaction mixture was heated at 150°C for 5 h. The progress of the reaction was monitored by TLC using AcOEt-hexane, 1:1, as eluent. The reaction mixture was cooled and quenched with ice water, and stirred for 30 min. Then the obtained solid was filtered off, and water was removed by azeotropic distillation with PhMe to get 4.00 g (73%) of compound 3. Mp 270-272°C. 1H NMR spectrum (300 MHz), δ, ppm (J, Hz): 7.04 (2H, s,NH2); 7.37 (1H, d, J = 9.0, H Ar); 7.78 (1H, dd, J = 9.0,J = 2.4, H Ar); 8.05 (1H, d, J = 2.4, H Ar); 9.09 (1H, s,H Ar). Mass spectrum, m/z: 225 [M+H]+.

References:

Babu, D. Suresh;Srinivasulu, Doddaga;Kotakadi, Venkata S. [Chemistry of Heterocyclic Compounds,2015,vol. 51,# 1,p. 60 - 66][Khim. Geterotsikl. Soedin.,2015,vol. 51,# 1,p. 60 - 66,7]

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