1-Phenethylamine, (-)- → HCID 15136845, compound

Participants

Reaction Steps

To a solution of (S)-1-phenylethylamine (2.6 mL) in THF (20 mL) at room temperature was added 2,4,6-trichloropyrimidine (1.83 g) dissolved in THF (10 mL) dropwise. The reaction mixture was stirred for 2 h, and then the solid was filtered and washed thoroughly with EtOAc. Combined filtrate was concentrated under reduced pressure, and the crude product was purified by flash chromatography (silica, 1:2), followed by 1:6 EtOAc:hexanes) to give 2-[(S)-1-phenylethylamino]-4,6-dichloropyrimidine (1.2 g) and 4-[(S)-1-phenylethylamino]-2,6-dichloropyrimidine (1.5 g). 2-[(S)-1-phenylethylamino]-4,6-dichloropyrimidine 1H NMR (500 MHz, CDCl3): δ 7.4-7.25 (m, 5H); 6.6 (s, 1H); 5.65 (br s, 1H); 5.2 (m, 1H); 1.58 (d, J=7.1 Hz, 3H). Mass spectrum (CI) 268.2 (M+1). 4-[(S)-1-phenylethylamino]-2,6-dichloropyrimidine 1H NMR (500 MHz, CDCl3): δ 7.41-7.3 (m, 5H); 6.1 (br s, 1H); 5.8 (br s, 1H); 4.6 (br s, 1H); 1.6 (d, J=7.1 Hz, 3H). Mass spectrum (CI) 268.2 (M+1).

Provenance & Evidence