Diisobutylaluminum hydride → [4-Cyclopropyl-6-methoxymethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.86 g (7.8 mmol) 4-cyclopropyl-6-methoxymethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid methyl ester in 30 ml tetrahydrofurane was dropped at −78° C., 20 ml (24 mmol) of a DIBALH-solution (1.2 M in toluene). The reaction was stirred for 15 min at −70° C., then the dry-ice bath was removed, the reaction temperature was allowed to come to RT and the solution was stirred for 2 h at RT. To the reaction mixture was then dropped carefully, under ice-cooling, 13 ml of 6N HCl. The reaction mixture was then taken up in ether and was washed with water. The ether-phase was concentrated under reduced pressure providing 1.29 g of pure crystalline [4-cyclopropyl-6-methoxymethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol.

Provenance & Evidence