5-BROMO-2-METHYL-PYRIMIDINE

A mixture of compound 5-bromo-2-methylpyrimidine-4-carboxylic acid (350 mg, 1.6 mmol) in xylene (5 mL) was refluxed for 2 h. After cooling, the mixture was applied directly to a silica column, which was eluted with petroleum ether, then ethyl acetate in petroleum ether (5percent v/v) to give compound 0601-120 (170 mg, 61 >) as a white solid. LCMS: 173 [M+l]A mixture of compound 5-bromo-2-methylpyrimidine-4-carboxylic acid (350 mg, 1.6 mmol) in xylene (5 mL) was refluxed for 2 h. After cooling, the mixture was applied directly to a silica column, which was eluted with petroleum ether, then ethyl acetate in petroleum ether (5percent v/v) to give compound 0601-120 (170 mg, 61percent) as a white solid. LCMS: 173 [M+1]A mixture of xylenes (5 mL) solution of compound 5-bromo-2-methyl-pyrimidine-4-carboxylic acid (350mg, 1.6mmol) was refluxed for 2 hours. After cooling, the mixture directly subjected to a silica column, petroleum ether, and then give the compound 0601-120 eluting with ethyl acetate in petroleum ether (5percent v / v) as a white solid (170mg, 61percent).A solution of KR-i 3 (i .46 g, 6.76 mmol) in xylene (20 mL) was heated iSO 00 for i6 h. After cooling to r.t., the mixture was purified by column to give thedesired product KR-i4 (0.3 g, 27.3percent) as a pale yellow solid. ESI-MS (M+i):i73calc.forC5H5BrN2: i72.0.Preparation 70 5-bromo-2-methylpyrimidine A solution of 5-bromo-2-iodopyrimidine (400 mg, 1.404 mmol), MesAl (2 M in toluene, 1053 μ, 2.106 mmol) and tetrakistriphenylphosphinepalladium(O) (32.5 mg, 0.028 mmol) in dioxane (4680 μΚ) was heated at 1 10 °C for 12 h. Water was added and the aqueous layer was extracted with EtOAc (x3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered, and the filtrate was evaporated in vacuo to give 5-bromo-2-methylpyrimidine (88 mg, 0.509 mmol, 36.2 percent yield) as a brown solid. NMR (500MHz, CHLOROFORM-d) δ 8.70 (s, 2H), 2.71 (s, 3H). MS (M+H)Under Ar(g), to a mixture of pyrazin-2-amine (1) (151 mg, 1.6mmol), 5- bromo-2-methylpyrimidine (2) (250mg, 1.4mmol), Cs2C03 (0.94g, 2.9mmol) was added degassed dry 1 , 4-dioxane (13mL). The reaction mixture was then flushed with Ar(g) for 1 min before Pd2(dba)3 (66mg, 0.07mmol) and Xantphos (92mg, 0.16mmol) were added. The reaction mixture was heated up to 90C for 40h. It was then cooled down to rt and concentrated in vacuo, CH2CI2 (15ml_) and H20 (15mL) were added. The organic phase was separated and the water layer 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 (54mg, 20%).To a stirred solution of To a solution of 5- bromo-2 -methyl-pyrimidine (700 mg, 4.05 mmol) and tetrahydropyran-4-amine (818 mg, 8.09 mmol) in toluene (12 ml) was added BINAP (504 mg, 0.81 mmol), Pd(OAc)2 (91 mg, 0.40 mmol) and Cs2C03 (2.64 g, 8.09 mmol). The mixture was stirred under N2 at 100 °C for 3 h. (1528) The mixture was poured into ethyl acetate (100 ml) and washed with 10: 1 H20 / methanol (4 x 100 ml). The EtOAc phase was concentrated in vacuo. The residue was purified by FCC (33 - 100 percent EtOAc in petroleum ether) to give the title compound as a white solid (Y = 45 percent). H NMR (400 MHz, chloroform-J) d ppm 8.07 (s, 2H), 4.05 - 3.95 (m, 2H), 3.57 - 3.48 (m, 3H), 2.61 (s, 3H), 2.06 - 2.00 (m, 2H), 1.55 - 1.44 (m, 2H).

A disubstituted pyrimidine derivative with strong insecticidal effects on house flies.

Molecular Weight:173.01
XLogP3:1.3
Hydrogen Bond Acceptor Count:2
Exact Mass:171.96361
Monoisotopic Mass:171.96361
Topological Polar Surface Area:25.8
Heavy Atom Count:8
Complexity:68.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes