Potassium Carbonate → HCID 44156896, compound

Participants

Reaction Conditions

Reaction Steps

50 ml of dimethylformamide was charged into a 250 ml 4 necked round bottom flask, connected to a mechanical stirrer, thermometer socket, condenser, addition funnel and nitrogen gas bubbler. 10.0 g (20.60 mmol) of (2,3-Dihydro-benzo[1,4]dioxin-6-yl methyl)-[1-(3-iodo-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amine (Compound No. 25), 14.50 g (0.146 mol) of ethynyl trimethyl silane, 46.0 mg of palladium acetate hexakis(acetato)tri palladium (II) 108.0 mg of triphenyl phosphine and 20.6 ml of triethyl amine were charged. Maintained the mass temperature at 25-35° C. for 30-45 min. Reaction mass temperature was raised to 80-85° C. Maintained the mass temperature at 80-85° C. for 4 hours. Reaction mass temperature was cooled to 50-55° C. and maintained for 2 hours. Reaction mass temperature was cooled to 25-30° C. and maintained for overnight under stirring. Solvent was completely distilled off under vacuum. The crude oil present was dissolved in 160 ml of water and compound was extracted with 300 ml of chloroform. Organic layer was dried with sodium sulphate. Sodium sulphate was filtered and washed the sodium sulphate with 50 ml of chloroform. Distilled off chloroform completely under vacuum. 9.50 g Of crude oil (Compound No. 13) was obtained. Compound was characterized by Mass spectrum [455 (M+1)]. 9.0 g of crude oil was dissolved in 85 ml of methanol and 85 ml of chloroform mixture. 11.30 g of potassium carbonate was added. Maintained the mass temperature at 25-35° C. for 14 hours. Distilled of the solvent completely under vacuum. 7.50 g Of crude oil was obtained. Crude oil was purified by the column chromatography with hexane and ethyl acetate mixture as mobile phase. Obtained 3.60 g (yield; 45.70% by theory) of product.

Provenance & Evidence