2-Chloro-5-methoxypyrimidine

off-white powder

Intermediate 3: 2-Chloro-5-methoxypyrimidine2, 4-Dichloro-5-methoxypyrimidine (43g, 0.24mol), zinc dust (86g, 1.32mol), ethanol (200 mL) and water (200 mL) were heated under reflux for 4h. The hot mixture was filtered and the ethanol was removed under reduced pressure. After cooling, the product was collected in ether. Recrystallisation from light petroleum (b.p.: 40-60°C) gave 2-chloro-5-methoxypyrimidine (20g, 58percent).Intermediate 3: -Chloro-5-methoxypyrimidine2, 4-Dichloro-5-methoxypyrimidine (43g, 0.24mol), zinc dust (86g, 1.32mol), ethanol (200 mL) and water (200 mL) were heated under reflux for 4h. The hot mixture was filtered and the ethanol was removed under reduced pressure. After cooling, the product was extracted into diethyl ether. Recrystallisation from light petroleum (b.p.: 40-60°C) gave 2-chloro-5-methoxypyrimidine (20g, 58percent).Mass: (ES+) 145 (M+H) (0.150 g, 1.038 mmol) was added to a 50 mL round bottom flask.Norfloxacin(0.331g, 1.038mmol)And potassium carbonate (0 · 172g, 1 · 246mmol), then add 10mL acetonitrile, Reflow at 80 ° Ctwenty fourhour.After the reaction, The reaction mixture was concentrated under reduced pressure to give a crude material.Then use the eluent (methanol / dichloromethane, 1/10, V/V)Purified by silica gel column chromatography, 0.215 g of compound 1-4 were obtained, It is a yellow solid. Yield: 50.3percentTo a 50 mL round bottom flask was added To 50mL In the round bottom flask Under Ar(g), to a mixture of pyrazin-2-amine (1) (289mg, 3.0mmol), 2- chloro-5-methoxypyrimidine (2) (289mg, 2.0mmol), Cs2C03 (1.30g, 4.0mmol) was added degassed dry 1 , 4-dioxane (13ml_). The reaction mixture was then flushed with Ar(g) for 1 min before Pd2(dba)3 (92mg, 0.1 mmol) and Xantphos (127mg, 0.22mmol) were added. The reaction mixture was heated up to 90C for 40h. It was then cooled down to rt. EtOAc (15ml_), H20 (10ml_) and brine (5mL) were added to the reaction mixture. The organic phase was separated and the aqueous phase was extracted with EtOAc (15ml_). The organic layers were combined and Pd-scavenger (MP-TMT, ~400mg, 1.3mmol/g) was added. This was shaken for several hours followed by filtration. The filtrate was concentrated in vacuo, dissolved in DMSO (4ml_) and purified by basic prep LCMS to yield (3) as a solid (70mg, 17%

Molecular Weight:144.56
XLogP3:1.1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:144.0090405
Monoisotopic Mass:144.0090405
Topological Polar Surface Area:35
Heavy Atom Count:9
Complexity:83
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes