Electric Literature of 1127-85-1, A common heterocyclic compound, 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, molecular formula is C8H8Cl2N2, its 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.
Step C: Synthesis of (2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yl)-methyl-amine. To a solution of 2,4-dichloro-5,6,7,8-tetrahydro-quinazolin (8.70 g, 42.8 mmol) in THF (87 mL) was added 40% aqueous MeNH2 (8.32 g, 107 mmol). The mixture was stirred at ambient temperature for 8 hr. The solution was poured into saturated aqueous NaHCO3 and the aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtrated, concentrated, and purified by flash chromatography (NH-silica, 50% EtOAc in hexane) to give (2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yl)-methyl-amine (7.04 g, 83%) as a white solid. ESI MS m/e 220, M + Na+; 1H NMR (300 MHz, CDCl3) delta 1.74-1.92 (m, 4 H), 2.26 (t, J= 5.5 Hz, 2 H), 2.67 (t, J= 5.6 Hz, 2 H), 3.05 (d, J= 5.0 Hz, 3 H), 4.81 (s, 1 H).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; Taisho Pharmaceutical Co. Ltd.; Arena Pharmaceuticals, Inc.; EP1464335; (2004); A2;,
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