2,5-Dichloro-4-methylpyrimidine

Intermediate 13: 2, 5-Dichloro-4-methylpyrimidine.To a solution of 2 , 4, 5-trichloropyrimidine (2.52 g, 13.74 mmol) in THF/NMP (86 mL/6 mL) was added Fe(acac)3 (485 mg, 1 .37) and the mixture was cooled to 0 C. 3.0 M MeMgBr in Et2O (6.87 mL, 20.61 mmol) was added dropwise. After 30 min at 0 C, the reaction was complete and quenched with saturated aqueous NH CI solution. Et2O was added and the layers were separated and the aqueous layer was further extracted with several portions of Et2O. The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (Hex to 10percent EtOAc/Hex) gave the desired product as a white solid (1 .45 g, 65percent). 1 H NMR (500 MHz, CDCI3): 8.47 (s, 1 H), 2.61 (s, 3H).2, 4, 5-Trichloropyrimidine (250 mg, 1.36 mmol) and ferric acetylacetonate (24 mg, 0.07 mniol) were taken up in tetrahydroruran (2.7 ml) and the reaction was cooled to -78 °C.Methylmagnesium bromide (0.45 ml of 3 M in THF, 1.36 mmol) was added dropwise and the mixture was stirred at -78 °C for one hour. The mixture was quenched with aqueous ammonium chloride and extracted with ethyl acetate. The combined organic fractions were dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by Combiflash (0-10percent diethylether in hexanes) to provide 2, 5- dichloro-4-methylpyrimidine (99 mg, 0.61 mmol, 45 percent) as a white solid. MS APCI: [M+H]

Molecular Weight:163.00
XLogP3:2.2
Hydrogen Bond Acceptor Count:2
Exact Mass:161.9751535
Monoisotopic Mass:161.9751535
Topological Polar Surface Area:25.8
Heavy Atom Count:9
Complexity:99
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes