2-[(6-methoxy-4-methylquinazolin-2-yl)amino]-1H-quinazolin-4-one synthesis
- Product Name:2-[(6-methoxy-4-methylquinazolin-2-yl)amino]-1H-quinazolin-4-one
- CAS Number:263746-98-1
- Molecular formula:C18H15N5O2
- Molecular Weight:333.34
Yield:263746-98-1 64%
Reaction Conditions:
in dimethyl sulfoxide at 170;
Steps:
4 2.1.4 2-((6-Methoxy-4-methylquinazolin-2-yl) amino) quinazolin-4(3H)-one (12b)
A mixture of 11a (0.05?g, 0.22?mmol) and anthranilic acid (0.04?g, 0.26?mmol) in 1?mL of DMSO was heated at 170?°C until the starting material disappeared.
The reaction mixture was cooled, water was added, and the resulting product was filtered and washed with excess water.
The crude mixture was recrystallized from chloroform to yield the desired product as colorless crystals (0.046?g, 64%).
1H NMR (600?MHz, DMSO-d6) δ 13.60 (s, 1H), 11.11 (s, 1H), 8.04 (d, J?=?7.7?Hz, 1H), 7.77-7.69 (m, 2H), 7.60 (dd, J?=?9.1, 2.7?Hz, 1H), 7.47 (t, J?=?7.6?Hz, 2H), 7.30 (t, J?=?7.4?Hz, 1H), 3.92 (s, 3H), 2.89 (s, 3H). HRMS-ESI (+) m/z calculated for C18H16N5O2, 334.1304 [M?+?H]+; found: 334.1307.
Adapted from (
Shikhaliev et al., 2003
).
References:
Ribeiro, Carlos J.A.;Kankanala, Jayakanth;Shi, Ke;Kurahashi, Kayo;Kiselev, Evgeny;Ravji, Azhar;Pommier, Yves;Aihara, Hideki;Wang, Zhengqiang [European Journal of Pharmaceutical Sciences,2018,vol. 118,p. 67 - 79]
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