4-CHLORO-6-METHOXY-5-NITROPYRIMIDINE

Sodium methoxide (2.70 g, 50.0 mmol) was added portionwise over 10 min to a 0°C suspension OF 4, 6-DICHLORO-5-NITROPYRIMIDINE (4.85 g, 25.0 mmol) in methanol (90 ml). On complete addition the mixture was stirred at 0°C for 2 h. The precipitate was filtered and the filtrate evaporated. The residue was suspended in isohexane and filtered. The filtrate was evaporated and the residue purified by flash column chromatography on silica, eluting with 5percent ethyl acetate in isohexane. Collecting appropriate fractions gave 4-chloro-6-methoxy-5- nitropyrimidine (3.50 g, 74percent) as a white solida)a) 4-Chloro-6-methoxy-5-nitropyrimidineSodium methoxide (2.94 g, 54.4 mmol) was added portion wise to a cooled (ice-bath) stirred suspension of 4, 6-dichloro-5-nitropyrimidine (5.00 g, 25.8 mmol) in anhydrous methanol (90 mL). After 4 hours stirring at 0 °C the mixture was filtered and the filtrate was concentrated in vacuo. The mixture was suspended in hexane, refiltered and the filtrate was concentrate to give an oil which was purified by flash chromatography (5:1 hexanes/ethyl acetate) to give the title compound (1 .97 g, 40percent) as a yellow solid.LRMS (m/z): 190 (M+1 )

Molecular Weight:189.56
XLogP3:1.3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:188.9941187
Monoisotopic Mass:188.9941187
Topological Polar Surface Area:80.8
Heavy Atom Count:12
Complexity:174
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes