3,4-Dichlorobenzyl alcohol → 2-(3,4-Dichlorobenzyloxy)-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine

Participants

Reaction Steps

2-Methylthio-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine (from Reference Example 3) was reacted with 3,4-dichlorobenzyl alcohol according to the procedures described in Example 1 to afford 2-(3,4-dichlorobenzyloxy)-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine as the higher Rf product (95/5 hexane/ethyl acetate TLC). HPLC/MS: m/e=511 (M+); Rt=5.07 min; 1H-NMR 500 MHz (CDCl3): δ 5.47 (s, 2H), 7.04 (d, J=9 Hz, 2H), 7.21 (d, J=9 Hz,1H), 7.22-7.30 (m, 3H), 7.38 (m, 2H), 7.43 (d, J=9 Hz, 1H), 7.66 (d, J=2 Hz,1H), 8.61 (s, 1H). 2-(3,4-Dichlorobenzyloxy)-4-(2-chloro-4-thiomethyl-phenyl)-5-(4-chlorophenyl)pyrimidine was obtained as the lower Rf product which was the by-product of the thiomethyl anion displacement of the 4-chloro substituent on the 4-(2,4-dichlorophenyl) ring. HPLC/MS: m/e=523 (M+1); Rt=4.93 min; 1H-NMR 500 MHz (CDCl3): δ 2.52 (s, 3H), 5.48 (s, 2H), 7.0-7.10 (m, 1H), 7.15-7.21 (m, 2H), 7.24-7.30 (m, 3H), 7.40-7.60 (m, 3H), 7.68 (d, J=2 Hz,1H), 860 (s, 1H).

Provenance & Evidence