4-Methoxy-2-pyrimidinamine

4-Chloro-6-methoxy-pyrimidin-2-ylamine (2.00, 12.58mmol) was dissolved in ethanol: ethyl acetate mixture (1 :1.3 ratios) to which was added di/sopropylethylamine (4.35ml, 25.2 mmol) and 10molpercent of 10percentPd-C. The reaction mixture was stirred under a positive hydrogen pressure using a hydrogen balloon for 14h. TLC was used, to follow the completion of the reaction (solvent 1 :1 ; hexane: ethyl acetate). The reaction mixture was flushed with nitrogen and then filtered off the palladium carbon over a celite bed. The bed was washed thoroughly with ethyl acetate. The filtrate was dried over anhydrous NaTo a solution of 4-chloro-6-methoxypyrimidine-2-ylamine (4.4 g, 27.7 mmol) in EtOAc (200 mL) and ethanol (150 mL), was added diisopropylethylamine (9.6 mL, 55.3 mmol) and 10percent palladium on carbon (2.9 g, 2.77 mmol). The heterogeneous solution was stirred under a balloon atmosphere of H0263] To a solution of 4-chloro-6-methoxypyrimidine-2-ylamine (4.4 g, 27.7 mmol) in EtOAc (200 mL) and ethanol (150 mL), was added diisopropylethylamine (9.6 mL, 55.3 mmol) and 10percent palladium on carbon (2.9 g, 2.77 mmol). The heterogeneous solution was stirred under a balloon atmosphere of HNa (2.2 g, 92.6 mmol) was dissolved in 30 mL of methanol. To this solution was added 7 (6.0 g, 46.3 mmol) in small portions at 5 °C. When the addition was complete, this mixture was heated to reflux for 4 h. After cooling, then the solvent was evaporated. The residue was dissolved in 30 mL of hydrochloric acid solution (20percent by weight) and filtered. The filtrate was alkalified with 10 mol/L sodium hydroxide solution to pH 9. After seeding and stirring for 1 h, the crystalline precipitate of the pyrimidinamine 8a which formed was filtered off and dried at about 60 °C. The yield was 84percent, m.p. 117-119 °C.4-Chloropyrimidin-2-amine (200 mg, 1.54 mmol) was dissolved in methanol (2 mL), and the mixture was stirred with heating at 110°C for 1 hr in a microwave synthesizer. Saturated aqueous sodium hydrogen carbonate solution was added to the mixture, and the mixture was extracted 3 times with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate, and concentration under reduced pressure to give 4-methoxypyrimidin-2-amine (140 mg, 73percent). ESIMS m/z: 126 (M + H)

Molecular Weight:125.13
XLogP3:0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:125.058911855
Monoisotopic Mass:125.058911855
Topological Polar Surface Area:61
Heavy Atom Count:9
Complexity:88.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes