Hydrochloric Acid → HCID 57531599, compound

Participants

Reaction Conditions

Reaction Steps

To a flask containing 2-(2,6-diethylphenyl)-6-methyl-5-({methyl[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}methyl)pyrimidine-4-carbonitrile (50 mg, 0.118 mmol) in toluene (5.0 mL) is cooled to 0° C. using an ice bath. DIBAL (0.354 mL of a 1.5 M solution in toluene, 3.0 eq., 0.53 mmol) is then added and the reaction is allowed to proceed for 3 h warming to room temperature. HCl (1.0 M 1.0 mL) is added and allowed to stir for 10 min, followed by basification with NaOH (5N). EtOAc (20 mL) is added and the organic layer is washed with NaHCO3 (10%, 100 mL), brine (100 mL) and dried over Na2SO4. SiO2 plate chromatography eluting with 20:1 CHCl3:MeOH affords the title compound as a white foam. [mass expected (428.61); mass found (428.38)].

Provenance & Evidence