2-Chloro-4-methoxy-6-methylpyrimidine

To a solution 2-amino-4-methoxy-6-methylpyrimidine (5 g, 35.97 mmol) in aqueous concentrated HCl (50 ml) was added NaNO[00223] To a solution of 2, 4-dichloro-6-methylpyrimidine (1 g, 6.14 mmol) in THF (10 ml) was added 0.5M NaOMe in MeOH (18.4 ml, 9.20 mmol) at 0 °C and stirred at r.t. overnight. A further 0.5 equivalents of 0.5 M NaOMe in MeOH (6.14 ml, 3.07 mmol) were added at 0 °C and the reaction stirred at r.t. for 1 h. The reaction mixture was diluted with water (30 ml) and extracted with EtOAc (2 x 50 ml). The combined organic extracts were washed with brine (20 ml), dried and concentrated in vacuo and the residue purified via column chromatography (100:0 - 75:25 Heptane-EtOAc) to afford the title compound (275 mg, 28percent) as a colourless crystalline solid. [00224] Method A: LC-MS m/z = 158.9 [M + H][00223] To a solution of 2, 4-dichloro-6-methylpyrimidine (1 g, 6.14 mmol) in THF (10 ml) was added 0.5M NaOMe in MeOH (18.4 ml, 9.20 mmol) at 0 C and stirred at r.t. overnight. A further 0.5 equivalents of 0.5 M NaOMe in MeOH (6.14 ml, 3.07 mmol) were added at 0 C and the reaction stirred at r.t. for 1 h. The reaction mixture was diluted with water (30 ml) and extracted with EtOAc (2 x 50 ml). The combined organic extracts were washed with brine (20 ml), dried and concentrated in vacuo and the residue purified via column chromatography (100:0 - 75:25 Heptane-EtOAc) to afford the title compound (275 mg, 28%) as a colourless crystalline solid. [00224] Method A: LC-MS m/z = 158.9 [M + H]+; RT = 1.05 min.The following compounds may particularly be mentioned as examples of these substances: ... 2-chloro-5-ethyl-pyrimidine 2-chloro-5-propyl-pyrimidine 2-chloro-5-isopropyl-pyrimidine 2, 4-dichloro-6-methyl-pyrimidine 2-chloro-4-methoxy-6-methyl-pyrimidine 2-chloro-4-amino-6-methyl-pyrimidine 2-chloro-4-methylamino-6-methyl-pyrimidine 2-chloro-4-dimethylamino-6-methyl-pyrimidine ...To a solution under nitrogen gas of compound 510-CN-I-1 (600 mg , 3.797mmol) in 1, 4-dioxane (15 ml), compound-3 (578 mg, 3.797mmol) and cesium carbonate (2.148 g, 6.592 mmol) were added. The resulting mixture was degassed 30 min with Argon gas, then Xantphos (440 mg, 0.759 mmol) and Pd2(dba) 3 (348 mg, 0.379 mmol) were added and the reaction mixture was stirred at 100C for 16 h. The reaction mixture was then cooled to room temperature, filtered and concentrated under reduced pressure. The residue was partitioned between brine and AcOEt and the aqueous layer was extracted with AcOEt. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a brown oil. The crude compound was purified by flash chromatography using (silica-gel: 100-200 mesh, AcOEt - petroleum ether; 70%) to give 0.3 g (yield 28.8%) of a pale yellow solid corresponding to 4- methoxy-6-methyl-N-(2-methyl-5-nitrophenyl)pyrimidin-2-amine. Mass: (ES+) C13H14N4O3 required 274.11; found 275.1 [M+H], HPLC/MS method 8.

Molecular Weight:158.58
XLogP3:1.9
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:158.0246905
Monoisotopic Mass:158.0246905
Topological Polar Surface Area:35
Heavy Atom Count:10
Complexity:112
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes