Phenethyl bromide → 2-Chloro-4-(N-(2-phenylethyl)anilino)pyrimidine

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Reaction Steps

2-Chloro-4-anilinopyrimidine (Reference Example A-9, 600 mg, 2.9 mmol) was dissolved in anhydrous DMF (8 ml) and sodium hydride (140 mg, 3.5 mmol, 60% in oil) was added portion wise. 10 min later phenethylbromide (478 μl, 3.5 mmol) was added and the mixture was stirred at ambient temperature for 5 hours. More sodium hydride (140 mg, 3.5 mmol, 60% in oil) and phenethylbromide (478 μl, 3.5 mnmol) were added and stirring was maintained overnight. The solvent was evaporated off and the residue partitioned between water and DCM. The organic phase was dried (MgSO4) the solvent evaporated. The crude product was purified by flash chromatography using first DCM then EtOAc/petroleum ether (25/75). The solvent was evaporated to give the title product as a white solid (530 mg, 59%). NMR (400 MHz, 353K): 2.90 (t, 2H), 4.10 (t, 2H), 6.15 (d, 1H), 7.25 (m, 7H), 7.45 (t, 1H), 7.65 (t, 2H), 8.00 (d, 1H); m/z: (ES+) 310 and 312 (MH+).

Provenance & Evidence