6-Amino-4-(3-chloro-4-fluoroanilino)quinazoline synthesis
- Product Name:6-Amino-4-(3-chloro-4-fluoroanilino)quinazoline
- CAS Number:184356-51-2
- Molecular formula:C14H10ClFN4
- Molecular Weight:288.71
184356-50-1
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Yield:184356-51-2 89%
Reaction Conditions:
with tin(II) chloride dihdyrate in ethyl acetate at 75; for 2 h;
Steps:
2.4 N-(3-chloro-4-fluorophenyl) quinazoline-4,6-diamine (16)
A mixture of 15 (1.1g, 0.0034mol) and SnCl2?2H2O (3.15 g, 0.014mol) was suspended in 35ml of ethyl acetate. The mixture was heated to reflux for 2 h. After completion of the reaction, the mixture was cooled to room temperature. The insoluble material was removed by filtration through Celite, and the filtrate was evaporated under reduce pressure. The resulting solid was recrystallized to give a white solid. 0.97g, (89%); mp 252~255°C; IR (KBr): 3387.34, 3143.05, 1627.35, 1613.65, 1578.01, 1495.33, 1454.76, 1366.18, 877.34, 849.19, 593.03; UV-VIS (CH3OH), λ/nm: 211, 237, 299, 366; 1H NMR (400 MHz, CD3OD): δ 8.32 (s, 1H), 8.01 (dd, J = 6.6, 2.3 Hz, 1H), 7.66 (dd, J = 7.8, 4.0 Hz, 1H), 7.57 (d, J = 8.8 Hz, 1H), 7.32 - 7.22 (m, 3H); ESI-MS for C14H10N4ClF [M+H]+: calcd: 288.71, found: 289.08; Anal. Calcd for C14H10N4ClF: C, 58.24; H, 3.49; N, 19.41. Found: C, 58.52; H, 3.68; N, 19.43.
References:
Wang, Zheng;Wu, Xue;Wang, Li;Zhang, Jiao;Liu, Jianli;Song, Zhongxing;Tang, Zhishu [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 11,p. 2589 - 2593] Location in patent:supporting information
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