Diisopropylethylamine → HCID 86697853, compound

Participants

Reaction Steps

A solution of 2,4-dichloro-5-trifluoromethyl-pyrimidine (7.5 g, 34.7 mmol) in dichloroethane and t-butanol (1:1, 10 mL) was treated with ZnCl2 (1M solution in ether, 35 mL) and stirred for half an hour at RT. The reaction mixture was cooled to 0° C. and a solution of ethyl propan-2-yl [(4-amino-3-methoxyphenyl) methyl]phosphonate (Compound 72E, 5 g, 16.28 mmol) in dichloroethane and t-butanol (1:1, 10 mL) followed by diisopropylethylamine (6 mL, 34.7 mmol) were added drop wise while stirring was continued for 24 hrs. The resulting white precipitate was filtered. The solid was dissolved in dichloromethane, washed with water (2×50 mL), dried over magnesium sulfate, filtered and evaporated to give 6.3 g of pure required isomer. 1H NMR (400 MHz, CDCl3) δ 8.6 (s, 1H), 8.32 (d, J=8.4 Hz, 1H), 8.04 (s, 1H), 7.04 (s, 1H), 6.89 (d, J=8 Hz, 1H), 4.73-4.76 (m, 1H), 4.08-4.11 (m, 2H), 3.95 (s, 3H), 3.23 (d, J=21 Hz, 2H), 1.24-1.33 (9H).

Provenance & Evidence