3,4-Dihydro-7-methoxy-4-oxoquinazolin-6-yl acetate

Brown solid powder

6-hydroxy-7-methoxy-3H-quinazolin-4-one (1.92 g, 10 mmol) was added to acetic anhydride (20 mL)Pyridine (4 mL) was added with stirring, Heated at 100 ° C for 4 hours.After cooling to room temperature, add ice water quenching reaction, The precipitated white solid was the intermediate M-1 (2.32 g, 99percent)To the reaction vessel were added 6-hydroxy-7-methoxy-4 (3H) -quinazolinone (4.8 g, 25 mmol), 20 mL of acetic anhydride, pyridinehaeating upto 100 degree celcius for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, the solvent was evaporated to dryness, and water was added to the residue to precipitate a solid. The resulting solid was washed with water, filtered and dried to give 6-ethoxycarbonyl-7-methoxy- Quinazolinone (2.26 g, yield 96.6percentStep 5. Step 5. 6-Acetoxy-7-methoxy-3, 4-dihydroquinazolin-4-one was obtained according to W096/33980 in 82percent yield. The crude product was used for the next step without purification.Into a reaction flask, acetic anhydride (864g, 16.25 m.eq) followed by 6-hydroxy- 7-methoxy-quinazoline-4(3H)-one of formula-XII (lOOg; 1.0 m.eq) were added under stirring and heated the reaction mass to 120-125°C and maintained for about 3h. The progress of the reaction was monitored by TLC. After completion of reaction, cooled the reaction mass to 25-35°C and quenched in ice water (2000g) under stirring. The resulting product mixture was heated to 60-65°C, maintained for lh and cooled the reaction mass to 25-35°C and maintained under stirring for 2h. The resulting product was isolated by filtration and washed with water. The product was further purified by recrystallization from dimethylformamide to afford 6-acetoxy-7-methoxy-quinazoline-4(3H)-one of formula-XV as crystalline solid (90.0g; 75percent by theory).The 6-hydroxy-7-methoxy -3H quinazolin-4-one (4g, 0.021mol), acetic anhydride (30 ml), pyridine (5 ml) and DMAP (10 mg) is added to the 50 ml reaction flask, stirring and heating to 100 °C, reaction 4h, by adding ice water, filtered, ice water washing, to obtain white powdery solid, yield 60percent.To a suspension of 6-hydroxy-7-methoxyquinazolin-4(3H)-one (0.57 g) and pyridine (4 mL) was added acetic anhydride ( 10 mL) at room temperature. The reaction mixture was stirred at 100 °C for 3 hours, and then poured into ice-water. The resulting mixture was filtered to give the title compound (0.40 g, 53.00 percent). The compound was characterized by the following spectroscopic data: ' NMR (400 MHz, dTo a suspension of 6-hydroxy-7-methoxyquinazolin-4(3H)-one (0.57 g) and pyridine (4 mL) was added acetic anhydride (10 mL) at room temperature. The reaction mixture was stirred at 100° C. for 3 hours, and then poured into ice-water. The resulting mixture was filtered to give the title compound (0.40 g, 53.00percent). The compound was characterized by the following spectroscopic data: Add 6-hydroxy-7-methoxy-3H-quinazolin-4-one (1 g, 5.2 mmol) in a 50 mL round bottom flask, acetic anhydride(20mL) and pyridine (4mL), the system was reacted at 100 ° C for 6h, The TLC detection of the starting material was complete.The reaction system was cooled to room temperature, and the round bottom flask was placed in an ice water bath and stirred.The suspension was then transferred to a 500 mL round bottom flask.In an ice water bath, add 300 mL of ice water and stir for 20 minutes.A large amount of white solid precipitated. Filter by suction, then wash the filter cake twice with water.Drying in an oven, the obtained white solid is (7-methoxy-4-oxo-3, 4-dihydroquinazoline)-6-yl-acetate, yield51percent.A mixture of 6-hydroxy-7-methoxyquinazolin-4(3H)-one (0103) (1O g crude), acetic anhydride (100 ml) and pyridine (8ml) was stirred and heated to reflux for 3 hours. The mixture was cooled to room temperature and poured into a mixture (250ml) of ice and water. The precipitate was isolated and dried to yield the title product 0104 as a grey solid (5.8g, 50percent two step overall yield): LCMS: m/z 235[M+1]A suspension of compound 3 (3.88 g, 20.2 mmol), pyridine (4 mL) and DMAP (122 mg, 1.0 mmol) in acetic anhydride (30 mL) was heated to 100 °C and stirred under NStep 2 a) To a solution of 8 (1.80 g, 8.73 mmol) in 11 mL of methanesulfonic acid, d, l-methionine was added (2.15 g, 14.4 mmol) and the mixture was stirred 24 h at 120 °C. The solution was cooled to room temperature and a solution of NaOH 2 M was added until precipitation. The solid was filtered, dissolved in 6.2 mL of acetic anhydride and pyridine (1.41 mL, 17.5 mmol) was added. The mixture was stirred 22 h at 100 °C. H(1-3) 7-methoxy-4-oxo-3, 4-dihydroquinazolin-6-yl acetate; 6.08 g of the compound obtained in (1-2) was dissolved in a mixture of 550 mi of acetic acid and 7 mi of pyridine, and the resulting solution was stirred 100

Molecular Weight:234.21
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:234.06405680
Monoisotopic Mass:234.06405680
Topological Polar Surface Area:77
Heavy Atom Count:17
Complexity:355
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes