1-(4-Pyrimidinyl)ethanone

2-BROMO-1-PYRIMIDIN-4-YLETHANONE hydrobromide The title compound was prepared by working as described in J. Med. Chem. 1992, 35, 3288. Onto a stirred solution of pyrimidine (2.5 g, 31.2 MMOLS) and acetaldehyde (10.8 mL, 192 mmols) in DICHLOROMETHANE (190 mL) at about 0°C, 3.4 M sulphuric acid (15.6 mL) was added dropwise. The solution was cooled TO-5°C and, from two distinct dropping funnels, two solutions were simultaneously dropped therein in about 30 minutes: an 80percent solution of tert- butylhydroperoxide in DI-TERT-BUTYLPEROXIDE/WATER (23.4 mL) and a solution of ferrous sulphate heptahydrate (52.2 g) in 100 mL of water. After addition, the reaction mixture was stirred at 0°C for 2.5 hours, then the phases were separated and the aqueous phase was extracted with DICHLOROMETHANE (2 x 150 mL). The joined organic phases were washed with a 10percent aqueous sodium iodide solution, with NAZIS205 (10percent aqueous solution) and with brine and then were dried over NA2S04. Upon concentration, the obtained yellow solid was taken up with petroleum ether and filtered. After drying, the title compound was obtained as a brownish solid (0.87 g, Y=23 percent).(iii) To a solution of N-methoxy-N-methylpyrimidine-4-carboxamide (2.25 g, 13.4 mmol)in dry THF (15 mL) at -55°C under nitrogen atmosphere, methyl magnesium bromide (5.4mL, 3 Msolution, 16.1 mmol) was added drop wise and allowed the reaction to reach roomtemperature. After TLC showed completion, quenched the reaction with saturated ammoniumchloride solution (10 mL) and extracted with EtOAc (3 x 25 mL). The combined organic layerwas dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude waspurified by column chromatography on silica gel (100–200 ) using 5percent EtOAc in hexane aseluent to afford 1-(pyrimidin-4-yl)ethan-1-one (225 mg, 14percent yield), as a white solid 1H NMR(400 MHz, DMSO-d6): δ 9.42 (s, 1H), 9.09 (d, J = 4.8 Hz, 1H), 7.90 (dd, J = 5.2, 1.2 Hz, 1H), 2.65 (s, 3H).

Molecular Weight:122.12
XLogP3:0.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:122.048012819
Monoisotopic Mass:122.048012819
Topological Polar Surface Area:42.8
Heavy Atom Count:9
Complexity:114
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes