2-Chloro-4-ethoxy-6-methyl-pyrimidine

Cs2CO3 (6.6 g, 20.2 mmol) and 46 mL of EtOH were added to 2, 4-dichloro-6-)pyrimidine (3.0 g, 18.4mmol), and the mixture was stirred for 48 hours under reflux. After filtering solids, the filtrate was purified by columnchromatography to obtain the title compound (1.88 g, 59 percent).1H-NMR (CDCl3) δ 6.47 (1H, s), 4.41 (2H, q), 2.42 (3H, s), 1.39 (3H, t)To a stirred solution containing 2.01 g (12.3 mmol) of 2, 4-dichloro-6-methylpyrimidine in 40 mL of anhydrous THF was added 927 mg (38.6 mmol) of NaH (60percent suspension in oil) and 392 μL (12.9 mmol) of EtOH. The reaction mixture was stirred at room temperature for 5 h and then poured slowly into 200 mL of water. The crude reaction mixture was extracted with two 300-mL portions of EtOAc. The combined organic phase was washed with brine, dried (MgSOTo a stirred solution containing 2.01 g (12.3 mmol) of 2, 4-dichloro-6-methylpyrimidine in 40 mL of anhydrous THF was added 927 mg (38.6 mmol) of NaH (60percent suspension in oil) and 392 jiL (12.9 mmol) of EtOH. The reaction mixture was stirred for 5 h at room temperature and then slowly poured into 200 mL of water. The crude was extracted with two 300-mL portions of EtOAc. The combined organic phase was washed with brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (15 x 6 cm). Elution with 19:1 hexane—EtOAc afforded 39 as a colorless solid: yield 2.16 g (51percent); mp 37-38 °C; silica gel TLC Rf 0.41 (4:1 hexane—EtOAc); ‘H NMR (CDC13, 400 MHz) 1.38 (t, 3H, J= 7.2 Hz), 2.42 (s, 3H), 4.42 (d, 2H, J= 7.2 Hz) and 6.46 (s, 1H); ‘3C NMR (CDCI3, 100 MHz) 14.4, 23.8, 63.5, 105.7, 159.8, 169.8 and 170.9; mass spectrum (APCI), m/z 173.0477 (M+H) (C7H10N2OC1 requires 173.0482).

Molecular Weight:172.61
XLogP3:2.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:172.0403406
Monoisotopic Mass:172.0403406
Topological Polar Surface Area:35
Heavy Atom Count:11
Complexity:123
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes