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A mixture of 3,3- dimethoxy-pyrrolidine (2.97 g, 17.8 mmol)and 4-chloro-6,7-dimethoxyquinazoline (4.38 g, 19.5 mmol) in THF (30 ml_)and satd. NaHCO3 (50 ml_) was heated to reflux for 5 h. The mixture was cooled and partitioned between water and ethyl acetate. The extract was washed with brine, and then extracted twice with 1 N HCI. After 20 min the combined acidic extracts were poured carefully into an excess of potassium carbonate in water. The mixture was then extracted three times with methylene chloride and the combined extracts were concentrated to a slurry. The slurry was diluted with an equal volume of hexanes and stirred over night. The EPO <DP n="41"/>resultant solids were collected via filtration and rinsed with ether to provide 3.71 g (76%) of the title compound as a tan powder. MS = 274.2.
4-(7-Bromo-3,4-dihydro-2H-quinolin-1-yl)-6,7-dimethoxy-quinazoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
11%
Example 103 4-(7-Bromo-3,4-dihydro-2H-quinolin-1-yl)-6,7-dimethoxy-quinazoline Utilizing a procedure analogous to that described in Example 1, this product was prepared in 11% yield from <strong>[114744-51-3]7-bromo-1,2,3,4-tetrahydroquinoline</strong> and 4-chloro-6,7-dimethoxy-quinazoline. (film; LC-MS: 399 (MH+)).
6,7-Dimethoxy-4-(5-methyl-2,3-dihydro-indol-1-yl)-quinazoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
94%
In isopropyl alcohol;
Example 23 6,7-Dimethoxy-4-(5-methyl-2,3-dihydro-indol-1-yl)-quinazoline Utilizing a procedure analogous to that described in Example 1, this product was prepared in 94% yield from <strong>[65826-95-1]5-methyl-indoline</strong> (1.1 eq.) and 4-chloro-6,7-dimethoxy-quinazoline (1.0 eq) in i-PrOH. (M.P. 180-181 C.; GC/MS: 321 (M+); anal. RP18-HPLC RT: 4.37 min.).
General procedure: A mixture of compound 2 (1.82 g, 8.8 mmol) and DMF (30 drops) in SOCl2 (50 mL) was refluxed for 7 h. The excess SOCl2 was removed by vacuum distillation. The residue was stirred with diethyl ether, filtered, washed, and dried to give compound 3 as a beige solid (1.83 g, 92%). A mixture of compound 3 and various amines in 2-propanol or DMF was refluxed. Upon completion of the reaction, it was cooled in an ice bath. The residue was filtered, washed, and dried to isolate the product.
With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 110℃; for 0.5h;Microwave irradiation;
General procedure: Preparation of compounds V: 241, V: 243-V: 245 A sample of 3H-spiro [isobenzofuran- 1 ,4?-piperidine] hydrochloride (1.2 equiv), corresponding 4-chloro quinazolines (1 equiv.) and DIEA (2 equiv.) was taken in a microwave vial and was added i-PrOH. The reaction mixture was heated to 110 °C for 30 mm in microwave. The solvents were concentrated in vacuo, the residue partitioned between EtOAc and H20, organic layer separated, washedwith sat. brine solution, dried over anhyd. Na2SO4, solvents removed in vacuo and the crude was purified by column chromatography to obtain desiredproducts in 3 5-70percent yields.
1-(6,7-imethoxyquinazolin-4-yl)indolin-4-ol hydrochloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
88%
In acetonitrile;Heating;
General procedure: 4-Chloro-6,7-dimethoxyquinazoline 3 and the required nucleophile were heated in solvent either thermally or using microwave heating until no further reaction was observed. On cooling, the hydrochloride salt was isolated by filtration. Alternative isolation procedures were employed if precipitation did not occur. Additional purification by preparative HPLC or flash column chromatography was employed in some cases. Spectroscopic data for compounds 4 [13], 6-9 [14-16], 20-21 [13], 25 [13], 28 [17] and 30 [18] are in agreement with those reported in the literature.
4-(2,4-difluoro-5-hydroxyanilino)-6,7-dimethoxyquinazoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Heating;
General procedure: 4-Chloro-6,7-dimethoxyquinazoline 3 and the required nucleophile were heated in solvent either thermally or using microwave heating until no further reaction was observed. On cooling, the hydrochloride salt was isolated by filtration. Alternative isolation procedures were employed if precipitation did not occur. Additional purification by preparative HPLC or flash column chromatography was employed in some cases. Spectroscopic data for compounds 4 [13], 6-9 [14-16], 20-21 [13], 25 [13], 28 [17] and 30 [18] are in agreement with those reported in the literature.
tert-butyl 7-(6,7-dimethoxyquinazolin-4-yl)-2,7-diazaspiro[3.5]nonane-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 16h;
[0513] Procedure: To a stirred solution of 4-chloro-6,7-dimethoxyquinazoline (0.2 g, 0.89 mmol) in DMF (10 mL) was added K2CO3 (0.184 g, 1.33 mmol) followed by <strong>[929302-18-1]2-(tert-butoxycarbonyl)-2,7-diazaspiro[3.5]nonan-7-ium hydrochloride</strong> (0.221 g, 0.979 mmol). Reaction mixture was stirred for 16 h at 90 °C. Progress of the reaction was monitored by TLC. Reaction mixture was diluted with water (20 mL), extracted with ethyl acetate (2 x 50mL). The combined organic layer was washed with brine (10mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The crude residue was purified by combiflash using ethyl acetate in hexaneto afford tert-butyl 7-(6,7- dimethoxyquinazolin-4-yl)-2,7-diazaspiro[3.5]nonane-2-carboxylate (0.3g, 81percent) as an off white solid. LC-MS (ES) m/z =415.2 [M+H]+.
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