Hydrochloric Acid → HCID 11350611, compound

Participants

Reaction Steps

A 2M solution of lithium borohydride in THF (22.4 ml, 44.8 mmol) was added to a mixture of 6-methoxycarbonyl-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine (Example 56) (4.0 mg, 8.96 mmol) in anhydrous THF (200 ml). The reaction mixture was stirred at ambient temperature for 3 hours and then heated at reflux for 1 hour. The mixture allowed to cool and methanol was added until effervescence ceased, a 4M solution hydrogen chloride in dioxane (30 ml) was then added and the mixture heated at reflux for 1 hour. The volatiles were removed by evaporation, the residue was dissolved in water and the resulting solution adjusted to pH 9 by careful addition of 10M aqueous sodium hydroxide solution. The aqueous mixture was extracted with DCM and purification by chromatography on silica gel, eluting with DCM/methanol (100:0 increasing in polarity to 90:10) to give the title compound (3.4 g, 91%).

Provenance & Evidence