Reference of 1127-85-1,Some common heterocyclic compound, 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, molecular formula is C8H8Cl2N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
This was prepared from MA2-10 (0.114 g) and MA3-034 (0.102 g) using procedure B (reaction time, 4 days). The volatiles were evaporated under the reduced pressure and the product was purified via column chromatography (Si02) eluting with hexanes/EtOAc (1:9 to 1 :2 v/v) to give the title compound MA3-064-1 as a gray solid (0.087 g, 44%). Mp: 265 C (dec). lH NMR (400 MHz, DMSO-ifc): delta 9.67 (s, 1H, disappeared on D20 shake), 8.73 (s, 1H, disappeared on D20 shake), 7.56 (s, 1H), 7.26-7.22 (m, 2H), 7.02-6.98 (m, 1H), 2.62 (t, / = 6.1 Hz, 2H), 2.47-2.43 (m, 2H, partially overlapped by residual DMSO solvent signal), 1.81-1.73 (m, 4H), 1.30 (s, 9H). NMR (400 MHz, CD3OD) delta 7.73-7.70 (m, 1H), 7.27-7.24 (m, 2H), 7.11-7.05 (m, 1H), 4.63 (s, 1H), 2.69 (t, / = 6.0 Hz, 3H), 2.55 (t, / = 6.0 Hz, 2H), 1.92-1.86 (m, 4H), 1.39 (s, 19H). HPLC-MS (ESI+): m/z 397.2 [40%, (M37C1+H)+], 395.2 [100%, (M35C1+H)+]. Procedure B A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, its application will become more common.
Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (293 pag.)WO2017/66428; (2017); A1;,
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