Ethanol → 4-Methyl-6-[4-(trifluoromethyl)phenyl]pyrimidine-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidine-2-carboxylate (which may be prepared by the method described in Description 29) (6.1 g, 20.59 mmol) in dry THF (120 mL) cooled to −75° C. was added diisobutylaluminium hydride (1M in toluene) (41.18 mL, 41.18 mmol) drop-wise over 10 minutes. The solution was stirred at the same temperature for 1.75 h then EtOH (0.96 ml) was added. After 1 minute the reaction mixture was poured into saturated Rochelle salt solution, (250 ml) and water (250 ml). EtOAc (250 ml) was added and the mixture stirred vigorously for 0.5 h then filtered under suction through celite. The filtrate was transferred to a separating funnel and the layers separated. The aqueous fraction was further extracted with EtOAc (200 ml) and the combined organic extracts were dried (MgSO4) and evaporated to a pale yellow, sticky solid. This was stirred with iso-hexane (30 ml) for 5 minutes then sonicated for 5 minutes. It was filtered, washed with iso-hexane (10 ml) and dried at RT under vacuum for 2 hours to give 4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidine-2-carbaldehyde (D30) (4.66 g);

Provenance & Evidence