2-Aminopyrimidine → HCID 68156882, compound

Participants

Reaction Steps

LiHMDS (1.0 M in tetrahydrofuran, 27.4 ml, 27.4 mmol) was added to 2-aminopyrimidine (1.43 g, 15.0 mmol) in tetrahydrofuran (50.0 ml) and stirred for 10 min. 2,4-Difluoronitrobenzene (1.50 ml, 13.7 mmol) was added and the reaction stirred for a further 15 min. The reaction mixture was quenched with water then poured into sodium bicarbonate (dilute aqueous) and the aqueous layer extracted with EtOAc (×3). The combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The product was purified by chromatography (SiO2, 0-100% EtOAc/cyclohexane) to yield the title compound (800 mg, 3.42 mmol, 25%). 1H NMR (CDCl3, 400 MHz): δ 8.94 (1H, dd, J 12.3, 2.4 Hz), 8.62 (2H, d, J=4.8 Hz), 8.36 (1H, dd, J 9.4, 6.1 Hz), 7.08 (1H, t, J=4.8 Hz), 6.88 (1H, ddd, J 9.6, 7.2, 2.8 Hz).

Provenance & Evidence