Carbon Dioxide → HCID 86673734, compound

Participants

Reaction Steps

A solution of (R)-5,5-difluoro-4-methyl-4-(1-(3-((trimethylsilyl)ethynyl)phenyl)-1H-pyrazol-4-yl)-5,6-dihydro-4H-1,3-oxazin-2-amine (68.6 mg, 177 μmol) in methanol (2 ml) was treated at room temperature with sodium methoxide (5.4M in methanol; 1 μl, 5.4 μmol). After 90 minutes a small quantity of dry ice was added to neutralize the reaction mixture. After evaporation at reduced pressure the residue thus obtained was dissolved in a mixture of water and dichloromethane. The aqueous layer was extracted with dichloromethane, thereafter, the combined organic layers were washed with water, dried over sodium sulphate, and evaporated. The residue was purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 0:100 as the eluent. The (R)-4-[1-(3-ethynyl-phenyl)-1H-pyrazol-4-yl]-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (29 mg, 52% yield) was obtained as a light yellow solid. MS (ISP): m/z=317.1 [M+H]+.

Provenance & Evidence