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With 2,3-Dimethylaniline; trichlorophosphate; In diethyl ether; water; toluene;
Part B The preparation of 4-chloro-5,6,7,8-tetrahydro-2-methylquinazoline To a mixture of 4.5 mL of phosphorus oxychloride and 20 drops of dimethylaniline in 50 mL of toluene was added 4.2 g of <strong>[19178-21-3]5,6,7,8-tetrahydro-2-methyl-4-quinazolone</strong>. The resulting mixture was refluxed for 3 hours and then cooled to room temperature. The reaction mixture was poured into a ice cold aqueous potassium carbonate. After stirring for 5 minutes the mixture was added to diethyl ether/water. The organic layer was recovered washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to yield a yellow oil. This oil was purified on silica to yield the desired compound as a light yellow solid (4.45 g, 95%): 1 H NMR (DMSO-d6, 300 MHz) delta 2.78 (m, 2H), 2.64 (m, 2H), 2.50 (s, 3H), 1.78 (m, 4H).
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl acetamide; at 90℃; for 16h;
A mixture of 4-chloro-2-methyl-5,6,7,8-tetrahydroquinazoline (0.183 g, 1mmol), <strong>[4410-12-2]1-benzyl-1,4-diazepan</strong> (0.228 g, 1.2 mmol), and N,N-diisopropylethylamine (0.35 mL, 2 mmol) in dimethylacetamide (7 mL) was stirred for 16 hours at 90C.Then the reaction mixture was cooled to room temperature and treated with brine (35mL). The mixture was extracted with ethyl acetate (2 x 70 mL). The combinedorganic layers were washed with water (70 mL), brine (70 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by HPLCchromatography (methanol/water) afforded 0.188 g (0.56 mmol, 56% yield) of Compound 31 as an oil. LS-MS (m/z): calcd./found for [M+H] 337.48/337.4.