4-chloro-2-methylquinazoline

Molecule 37 was prepared in two steps from commercial 2-methylquinazolin-4(3H)-one. This last was first chlorinated at position 4, by using POClTo a solution of 2-methylquinazolin-4(3H)-one (3.28 g, 20.50 mmol) in toluene (55 mL) was added N, N-diethyl aniline (4.92 mL, 30.74 mmol). 4-Chloro-2-methyl-quinazoline : A stirred suspension of 2-methyl-4 (3H) - quinazolinone (5 g, 31.2 mmol) in POCI3 (100 mL) was heated at 120°C for 3 h. The excess POC13 was removed under vacuum, then to the residue was added crushed ice and 200 mL of saturated NAHC03, and the mixture was extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water, saturated NACI, dried over anhydrous MGS04, filtered and concentrated. The crude product was purified by column chromatography (5-8percent ethyl acetate/hexane) to give the title compound (2.5 g, 14.0 mmol, 45percent). 1H NMR (CDC13) : 8.21-8. 25 (m, 1H), 7.89-7. 99 (m, 2H), 7.66 (ddd, 1H, J=1. 8, 6. 6, 8. 7), 2. 87 (s, 3H).A stirred suspension of 2-methyl-4(3H)- quinazolinone (5 g, 31.2 mmol) in POClA stirred suspension of 2-methy 1-4(3 H)- quinazolinone (5 g, 31.2 mmol) in POCl(4-Methoxy-phenyl)-methyl-(2-methyl-quinazolin-4-yl)-amine hydrochloride[0038] a) 4-Chloro-2-methyl-quinazoline: A stirred suspension of 2-methy 1-4(3 H)- quinazolinone (5 g, 31.2 mmol) in POCl[0030] a) 4-Chloro-2-methyl-quinazoline: A stirred suspension of 2-methyl-4(3H)- quinazolinone (5 g, 31.2 mmol) in POCl4-Chloro-2-methyl-quinazoline: A stirred suspension of 2-methy 1-4(3 H)- quinazolinone (5 g, 31.2 mmol) in POCl4-Chloro-2-methyl-quinazoline: A stirred suspension of 2- methyl-4(3H)-quinazolinone (5 g, 31.2 mmol) in POCl4-Chloro-2-methyl-quinazoline: A stirred suspension of 2-methyl-4(3H)- quinazolinone (5 g, 31.2 mmol) in POClStep-2; 4-Chloro-2-methylquinazoline; To a mixture of 2-methylquinazolin-4(3H)-one (9.2g, 0.0574mol) and phosphorous oxychloride (5.8g, 0.037mol) in dry toluene (250ml) was added N, N-dimethyl aniline (13.9g, 0.14mol) and the mixture was refluxed for 3h. The reaction mixture was cooled and washed with water, brine and dried. The solvent was removed under vacuum and the residue was purified by chromatography (silica gel, 60-120 mesh) eluting with pet ether/ ethyl acetate (9/1) to afford 4g (39percent) of the titled compound as a solid.LCMS: Mass found (M+l, 178.9),

Molecular Weight:178.62
XLogP3:3.2
Hydrogen Bond Acceptor Count:2
Exact Mass:178.0297759
Monoisotopic Mass:178.0297759
Topological Polar Surface Area:25.8
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes