5-BROMO-2-(METHYLAMINO)PYRIMIDINE

40percent Aqueous methylamine solution (35 ml) and methanol (20 ml) were added to 5-bromo-2-chloropyrimidine (3 g, 15.5 mmol) and the resulting mixture was heated to reflux for 3 days. The mixture was cooled, then the solvent was evaporated under reduced pressure, the residue was partitioned with methylene chloride and 1 M sodium hydroxide, the organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (3.0 g, 100percent) as a white solid.5-bromo-2-chloropyrimidine (2.00 g, 10.34 mmol), methylamine (41 percent in water, 2.00 mL, 23.78 mmol) and potassium carbonate (1.43 g, 10.34 mmol) in tert-butanol (4 mL)/THF (4 mL) are stirred for 15 min at 150[0238] Methylamine (2.0 M in methanol, 4O mL, 80 mmol) was added to 5- bromo-2-chloropyrirnidine (5.6 g, 29.0 mmol) in a sealable reaction vessel. After allowing to vent for a few minutes, the vessel was sealed, placed behind a safety shield and heated in a 115 Synthesis -Aminomethyl-5-bromopyrimidine[0083] Methylamine (2.0 M in methanol, 40 mL, 80 mmol) was added to 5-bromo-2- chloropyrimidine (5.6 g, 29.0 mmol) in a sealable reaction vessel. After allowing to vent for a few minutes, the vessel was sealed, placed behind a safety shield and heated in a 115 °C oil bath for 48 hours. Upon cooling the volatiles were removed in vacuo. The material was dissolved in CHTo 5-bromo-2-chloropyrimidine (2g, 10.34mmol) was added 1 M methylamine solution in THF (20ml). The contents were stirred at 6OStep 39a: 5-Bromo-N-methylpyrimidin-2-amine (compound 0601-116) and 5-bromo-N, N- dimethylpyrimidin-2-amine (compound 0601-117)A mixture of 5-bromopyrimidin-2-amine (3.48 g, 20 mmol) and DMF (20 mL) was cooled to 0°C. To the mixture NaH (60percent, 1.44 g, 36 mmol) was added. After 15 minutes, iodomethane (5 mL, 80 mmol) was added and stirred at 0°C for 0.5 h and the mixture was warmed to room temperature for additional 4 hours. Water (30 mL) was added and extracted with ethyl acetate (3 x 30 mL). The combined organic layers was washed with brine, dried over Na2S04, concentrated and purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10percent v/v) to give two compounds: compound 0601-116 (0.76 g, 20percent) as a white solid, LCMS: 190 [M+2]Step 39a: 5-Bromo-N-methylpyrimidin-2-amine (compound 0601-116) and 5-bromo-N, N-dimethylpyrimidin-2-amine (compound 0601-117)[0353]A mixture of 5-bromopyrimidin-2-amine (3.48 g, 20 mmol) and DMF (20 mL) was cooled to 0° C. To the mixture NaH (60percent, 1.44 g, 36 mmol) was added. After 15 minutes, iodomethane (5 mL, 80 mmol) was added and stirred at 0° C. for 0.5 h and the mixture was warmed to room temperature for additional 4 hours. Water (30 mL) was added and extracted with ethyl acetate (3×30 mL). The combined organic layers was washed with brine, dried over Na2SO4, concentrated and purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10percent v/v) to give two compounds: compound 0601-116 (0.76 g, 20percent) as a white solid, LCMS: 190 [M+2]5-bromo-pyrimidine-2-amine (3.48g, 20mmol) and a mixture of DMF (20mL) was cooled to 0 . NaH (60percent, 1.44g, 36mmol) to the mixture was added. After 15 minutes, then 0.5 hours with stirring at O ° C. was added iodoethane (5 mL, 80 mmol), the mixture was further warmed to room temperature for 4 hours. With the addition of water (30mL) and extracted with ethyl acetate (3x30mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated and purified by column chromatography (petroleum ether in ethyl acetate, 10percent v / v) on silica gel to give the two compounds: Compound 0601 the -116 as a white solid (0.76g, 20percent)

Molecular Weight:188.03
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:186.97451
Monoisotopic Mass:186.97451
Topological Polar Surface Area:37.8
Heavy Atom Count:9
Complexity:80.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes