2,4,5-Trichloroquinazoline

Substrate: Trichloroquinazoline. Experimental: Trichloroquinazoline (0.4 mmol, 93.4 mg) was combined with 2 equivalents K(i8-crown-6)(B3N3Me6CF3)(THF) (0.8 mmol, 4 mL, o.2M solution in THF) and stirred for 30 minutes at 25 C. One equivalent benzyl bromide (0.4 mmol, 68.4 mg) was then added, and the mixture stirred at 70 C for 24 hours. The reaction was then cooled to 25 C, and 1 equivalent sodium thiophenolate (0.4 mmol, 52.8 mg) was added. The reaction was then heated to70 C and stirred for 24 hours. The THF solvent was then removed by rotary evaporation, and the crude solid purified by flash chromatography (conditions: 5i02 column, o-o% DCM/Hexaneover 16 column volumes at a flow rate of 1 column volume per minute) to afford 120 mg of white solid (6o%). 1HNMR (CDC13): 7.55 (q, 2H, overlap), 7.54 (1H, a, overlap), 7.41 (H, x -r, , overlap), 7.34(1H, a, (t, J1H-1H7.4)), 7.28 (2H, , (d, J1H-1H7.7)), 7.24 (1H, (d(d), (J1H-1H=8.8, 2.1)), 6.75 (1H, y, (d, J1H-1H9.0)), 5.27 (2H, 6, s). 13CNMR: 158.99, 136.80, 135.69, 134.95, 130.81, 129.48, 129.37, 129.21, 128.73, 128.08, 127.93, 125.76, 122.46 (q, J13c19F=288), 115.67, 113.23, 66.8o(p, J13C-19F28.7), 50.36.19F-NMR: -73.92 (s). HRMS (ESI+): 501.0619 (M+H: 501.0621).297 mg (1.28 mmol) of compound A-1, 275 mg (1.28 mmol) of compound N- (3- (aminomethyl) pyridin-2-yl) -N-methylmethanesulfonamide and0.356 mL (2.56 mmol) of triethylamine was dissolved in 15 mL of dichloromethane, Stir at room temperature.After 4 h, the reaction was stopped, the solvent was evaporated under reduced pressure, The crude product was washed with ether, A white solid B-1 was obtained in a yield of 43.0%.General procedure: Phosphorus pentachloride (12.5 g, 60.0 mmol) and phosphorus oxychloride (46.00 mL, 502.50 mmol) were sequentially added to a 250 mL of a single jar, and6-fluoroquinazolin-2, 4- (1H, 3H) -dione(3.60 g, 20.00 mmol) was slowly added under stirring. The reaction mixture was gradually warmed to reflux and reacted. After the reaction of 9 h, the reaction mixture was cooled, the solvent was removed in vacuo, and the residue was slowly poured into a mixture of ice and water (400 mL) . After being stirred for 0.5 h, the resulting mixture was extracted with dichloromethane (250 mL x 3) . The combined organic layers were concentrated. The residue was purified by silica gel column chromatography eluted with (petroleum ether/ethyl acetate (v/v) 30/1) to give the title compound (as a white solid, 3.74 g, 86) .c) 134 mg (1.28 mmol) of ethyl carbazate were added to a solution of 200 mg. (0.85 mmol) of b) 0.5 g (2.54 mmol) of 5-chloro-1, 2, 3, 4-tetrahydroquinazoline-2, 4-dione was suspended in 7 ml (96 mmol) of phosphorus oxychloride and heated to 120 C. for 24 hrs. The reaction mixture was left to cool to room temperature and poured on to ice-water. The brown precipitate was filtered off, dried and chromatographed over silica gel with methylene chloride as the eluent. 260 mg (44%) of R-2, 5-dichloro-4-(2-hydroxy-1-methylethylamino)quinazoline, m.p. 180-182 C., from

Molecular Weight:233.5
XLogP3:4.1
Hydrogen Bond Acceptor Count:2
Exact Mass:231.936181
Monoisotopic Mass:231.936181
Topological Polar Surface Area:25.8
Heavy Atom Count:13
Complexity:190
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes