HCID 89825946, compound → HCID 89825765, compound

Participants

Reaction Conditions

Reaction Steps

In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (120mg, 0.51 mmol), N-(5-amino-2-((2-hydroxyethyl)(methyl)amino)phenyl)acetamide (115 mg, 0.51 mmol), and cesium carbonate (335 mg, 1.03 mmol) in DMA (3.0 mL) (),Pd2(dba)3 (23.51 mg, 0.03 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (29.7 mg, 0.05 mmol) were added. to give a brown suspension. The vial was filled with N2, 150C microwave for 30 min. LCMS showed SM and product. under microwave 150C for another 2h. 15% SM remained. MeOH (2 mL) was added to the reaction mixture. filtered. The mother liquid solvent was removed by ratovapor to yield stick oil. The crude product was loaded on ISCO (Hex to Hex:EtOAc To EtOAc to EtOAc:MeOH=10:1) to give sticky oil. The product was not pure. added 1 mL of EtOAc, the solid was promoted to form by scratching the flask wall. The resulting suspension was heated to reflux. When it was warm, the mixture was filtered to give offwhite solid. This solid was washed with EtOAc ( 2 mL) and dried at 80C under reduced press oven to give N-(5-(3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)-2-((2-hydroxyethyl)(methyl)amino)phenyl)acetamide (110 mg, 50.9 %) NMR and LCMS showed desired product, see attachment

Provenance & Evidence