Phosphorus oxychloride → HCID 178451808, compound

Participants

Reaction Conditions

Reaction Steps

Into a solution of tert-butyl 4-[5-(1,3-benzothiazol-2-yl)-4,6-dihydroxypyrimidin-2-yl]piperidine-1-carboxylate (45 g, 105.02 mmol, 1.00 equiv) in toluene (500 ml) was added phosphoryl trichloride (16.1 g, 105.00 mmol, 1.00 equiv) and N,N-Diisopropylethylamine (27 g, 209.30 mmol, 1.99 equiv). The resulting solution was stirred for 20 mins at 120° C. Upon concentrated under vacuum, the residue was purified by flash chromatography on a silica gel column eluting with ethyl acetate/petroleum ether (1:10) to give 30 g of tert-butyl 4-[5-(1,3-benzothiazol-2-yl)-4-chloro-6-hydroxypyrimidin-2-yl]piperidine-1-carboxylate as a light yellow solid. MS m/z [M+H]+ (ESI): 447.

Provenance & Evidence