N,N-Dimethylaniline → HCID 86696590, compound

Participants

Reaction Conditions

Reaction Steps

The methyl 2-(4-hydroxy-2-methylpyrimido[1,2-b]indazol-3-yl)acetate (1.34 g; 4.94 mmol) was suspended in phosphorus oxychloride (5.1 mL) and dimethylaniline (0.96 mL) was added under nitrogen atmosphere. The well-stirred reaction mixture was heated at 60° C. for 3 days. Phosphorus oxychloride in excess was removed under reduced pressure and the remaining oil was placed in an ice-bath. A cold saturated sodium hydrogenocarbonate solution was carefully added until neutralization. The aqueous layer was extracted with ethyl acetate, the organics were combined, dried over sodium sulfate, concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (1-20%) in dichloromethane furnished 0.659 g (46%) of methyl 2-(4-chloro-2-methylpyrimido[1,2-b]indazol-3-yl)acetate as a light yellow solid. ESI/APCI(+): 290-292 (M+H).

Provenance & Evidence