ChemicalBook CAS DataBase List 6-BROMO-2-QUINAZOLINAMINE

6-BROMO-2-QUINAZOLINAMINE synthesis

6synthesis methods

Product Name:6-BROMO-2-QUINAZOLINAMINE
CAS Number:190273-89-3
Molecular formula:C8H6BrN3
Molecular Weight:224.06

593-85-1

93777-26-5

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).

593-85-1 Synthesis

593-85-1
513 suppliers
$6.00/25g

93777-26-5 Synthesis

93777-26-5
371 suppliers
$5.00/5g

190273-89-3
135 suppliers
$55.00/250mg

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]

593-85-1 Synthesis

593-85-1
513 suppliers
$6.00/25g

93777-26-5 Synthesis

93777-26-5
371 suppliers
$5.00/5g

190273-89-3
135 suppliers
$55.00/250mg

References

420-04-2 Synthesis