Chloroform → HCID 58034329, compound

Participants

Reaction Conditions

Reaction Steps

To a 250 mL round bottom flask was added 2-methyl-7-phenylpyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-8(9H)-one (1-3) (3 g, 10.9 mmol, 1 eq.), CHCl3 (120 mL), SOCl2 (5.17 g, 3.17 mL, 43.5 mmol, 4 eq.) and DMF (158.9 mg, 168.3 uL, 2.17 mmol, 0.2 eq.). The mixture was heated to 70° C. in an oil bath for 1 h. After 1 h, additional SOCl2 (1.6 mL, 21.8 mmol, 2 eq.) and DMF (168.3 uL, 2.17 mmol, 0.2 eq.) were added. The mixture was maintained at 70° C. for an additional 2 h. After 3 h total, LCMS analysis and TLC analysis (heptane:EtOAc (3:7)) of the resulting light brown solution indicated that the reaction was complete. The reaction was concentrated in vacuo and the residue diluted with EtOAc (100 mL), washed with saturated aqueous NaHCO3 solution (50 mL), and the aqueous phases re-extracted with EtOAc (3×200 mL). The combined organic phases were dried over MgSO4, filtered, and concentrated to give 3.2 g of material which was purified by silica gel chromatography using EtOAc/heptane as the eluent to give 8-chloro-2-methyl-7-phenylpyrazolo[1,5-a]pyrido[3,2-e]pyrimidine (1-4) as an yellow solid.

Provenance & Evidence