Diethyl Ether → HCID 86697745, compound

Participants

Reaction Steps

A 1M solution of zinc chloride in ether (18.7 mL, 18.7 mmol) was added to a solution of 2,6-dichloro-5-trifluoromethylpyrimidine (4 g, 18.72 mmol) in 20 mL of dichloroethane and t-butanol (1:1) under nitrogen atmosphere. The reaction mixture was stirred at rt for 30 min, cooled to 0° C. and then treated slowly over 10 min with a solution of diethyl (4-amino-3-bromobenzyl)phosphonate (Compound 32D, 3.35 gm, 10.4 mmol) in dichloroethane and t-butanol (10 mL, 1:1) through an addition funnel and stirred for 1 hr. Diisopropylethylamine (3.2 mL, 10.4 mmol) was added and the mixture was allowed to stir at rt for 3 days. The solvents were evaporated and the residue was purified using flash column chromatography (0-30% EtOAc/DCM) to afford 1.2 g of the title compound (23%). 1H NMR (400 MHz, CDCl3): δ 1.23-1.25 (m, 6H), 3.10 (d, J=22.0 Hz, 2H), 3.99-4.06 (m, 4H), 7.28 (d, J=8.4 Hz, 1H), 7.52 (s, 1H), 7.8 (s, 1H), 8.26 (d, J=8.4 Hz, 1H), 8.57 (s, 1H).

Provenance & Evidence