N,N-Diethylaniline → HCID 86597652, compound

Participants

Reaction Conditions

Reaction Steps

To tert-butyl 3-[4-(7-cycloheptyl-5-hydroxy[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenoxy]propyl(methyl)carbamate (876 mg, 1.64 mmol) is added 5.8 mL of phosphorous oxychloride and 2.9 mL of N,N-diethylaniline, and the mixture is heated at 90° C. for 3 h. The excess phosphorous oxychloride is removed in vaccuo, and the resulting residue is diluted with ethyl acetate. The organic layer is washed with ice water and saturated sodium chloride (x2), dried over magnesium sulfate, and concentrated to a residue. The residue is chromatographed over silica gel, eluting with a gradient of hexanes to 40% ethyl acetate in hexanes. Concentration provides tert-butyl 3-[4-(5-chloro-7-cycloheptyl [1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenoxy]propyl(methyl)carbamate as a light yellow oil (452 mg). MS: m/z 550.1 (M+H).

Provenance & Evidence