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With thionyl chloride; In N,N-dimethyl-formamide; |
After repetition of the previous steps, a mixture of <strong>[179688-53-0]6-acetoxy-7-methoxy-3,4-dihydroquinazolin-4-one</strong> (15 g), thionyl chloride (215 ml) and DMF (4.3 ml) was stirred and heated to 90 C. for 4 hours. The mixture was cooled to ambient temperature and the thionyl chloride was evaporated. There was thus obtained 6-acetoxy-4-chloro-7-methoxyquinazoline, hydrochloride salt, which was used without further purification. |
|
With thionyl chloride; In N,N-dimethyl-formamide; |
After repetition of the previous steps, a mixture of 6-acetoxy-7-methoxy-3, 4-dihydroquinazolin-4-one (15 g), thionyl chloride (215 ml) and DMF (4.3 ml) was stirred and heated to 90 C. for 4 hours. The mixture was cooled to ambient temperature and the thionyl chloride was evaporated. There was thus obtained 6-acetoxy-4-chloro-7-methoxyquinazoline, hydrochloride salt, which was used without further purification. |
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With thionyl chloride; trichlorophosphate;N,N-dimethyl-formamide; at 120℃; for 7h; |
(1-4) 4-chloro-7-methoxyquinazolin-6-yl acetate hydrochloride salt; 4.87 g of the compound obtained in (1-3) was dissolved in a mixture of 33 mi thionylchloride and 6 mi of phosphorus oxychloride. Two drops of dimethylformamide were added to the resulting solution and stirred at 120 C for 7 hours. The reaction solution was cooled to room temperature and the solvent was removed therefrom under a reduced pressure, to obtain a residue. Toluene was added the residue, and the resulting solution was concentrated under a reduced pressure to remove the solvent, and this procedure was repeated 2 more times. The solid thus obtained was dried under a reduced <n="23"/>pressure to obtain the title compound (5.16 g).1 1HH--NNMMRR ((330000MMHHz, DMSO-d6) δ 9.01 (s, IH), 8.02 (s, IH), 7.64 (_?, IH), 4.02 (s, 3H), 2.35 (s, 3H). |
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With thionyl chloride; N,N-dimethyl-formamide; In chloroform; at 25℃; for 5h;Reflux; |
Into a reaction flask, chloroform (2100 mL), 6-acetoxy-7-methoxy-quinazoline-4(3H)- one of formula-XV (150. Og; 1.0 m.eq) and dimethyl formamide (45g; 0.96 m.eq) were added under stirring. To this, thionyl chloride (114.3g; 1.5 m.eq) was added dropwise at 25-35C. After addition, heated the reaction mass to reflux temperature and maintained for about 5h. The progress of the reaction was monitored by HPLC. After completion of reaction, reaction mixture was quenched with aqueous sodium bicarbonate solution under stirring and the resultant organic layer was separated. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure to afford (4-chloro-7-methoxy-quinazolin- (0135) 6- yl) acetate hydrochloride of compound of formula-XVI as pale yellow color wet solid. The wet product was purified by trituration with isopropyl alcohol, filtered and the wet solid (~280g) was used as such in the next stage without further drying. HPLC purity: >95.0% ii) |
| 5.16 g |
With thionyl chloride; trichlorophosphate; In N,N-dimethyl-formamide; at 120℃; for 7h; |
4.87 g of the compound obtained in (1-3) was dissolved in a mixture of 33 ml thionyichioride and 6 ml of phosphorus oxychloride. Two drops of dimethylformamide were added to the resulting solution and stirred at 1 20 00 for 7 hours. The reaction solution was cooled to room temperature and the solvent was removed therefromunder a reduced pressure, to obtain a residue. Toluene was added the residue, and the resulting solution was concentrated under a reduced pressure to remove the solvent, and this procedure was repeated 2 more times. The solid thus obtained was dried under a reduced pressure to obtain the title compound (5.16 g). 1H-NMR (300MHz, DMSO-d6) O 9.01 (s, 1 H), 8.02 (s, 1 H), 7.64 (s, 1 H), 4.02(s, 3H), 2.35 (s, 3H). |
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