Trifluoroacetic acid → HCID 18697949, compound

Participants

Reaction Steps

A solution of 4-(2-(4-tert-butoxycarbonylpiperazin-1-yl)pyrid-5-yl)-2-chloropyrimidine (8.00 g, 21.30 mmol) in dichloromethane (60 ml) was treated with trifluoroacetic acid and the resulting mixture stirred at room temperature for 2 h, then evaporated and reconcentrated four times from dichloromethane. The residue was suspended in a mixture of dichloromethane (150 ml) and saturated aqueous sodium bicarbonate (150 ml) then treated portionwise with benzyl chloroformate (4.00 g, 23.44 mmol) in dichloromethane (5 ml). The resulting mixture was stirred rapidly for 18 h then the organic phase was separated, dried (MgSO4) and evaporated to give the crude product which was purified by recrystallisation (ethyl acetate-hexane) to afford the title compound (7.85 g) as an off-white solid m.p. 145-147°. δH (CDCl3) 3.65-3.77 (8H, m), 5.18 (2H, s), 6.73 (1H, d, J 9.1 Hz), 7.36 (5H, m), 7.52 (1H, d, J 5.4 Hz), 8.31 (1H, dd, J 2.3, 8.1 Hz), 8.54 (1H, d, J 5.4 Hz) and 8.86 (1H, d, J 2.3 Hz).

Provenance & Evidence