Water → HCID 11154288, compound

Participants

Reaction Conditions

Reaction Steps

Sodium azide (44 mg, 0.68 mmol) was added to a solution of 6-[(4-methylphenylsulphonyloxy)methyl]-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-1-N-[4-methylphenylsulphonyl]-1H-pyrazol-3-ylamino)pyrimidine (Method 52) (159 mg, 0.22 mmol) in anhydrous DMF (2.0 ml) and the mixture heated at 110° C. for 1.5 hours. Triphenylphosphine (282.0 mg, 1.08 mmol) and water (0.10 ml) were then added and the reaction mixture heated at 100° C. for 1 hour. The mixture allowed to cool and was then passed through a 50 g isolute SCX-2 ion exchange column. The column was eluted with methanol to elute any neutrals, followed by 7M methanolic ammonia to elute the product. The volatiles were removed by evaporation and the residue dissolved in methanol (5 ml) and 10M aqueous sodium hydroxide solution (0.5 ml) and stirred for 1 hour. The volatiles were removed by evaporation and the residue dissolved in water, and extracted with DCM. The extracts were combined, the solvent removed by evaporation and the residue purified by chromatography on silica gel, eluting with DCM/methanol/aqueous ammonia (100:0:0 increasing in polarity to 80:20:1) to give the title compound (48.5 mg, 53%) as a solid.

Provenance & Evidence