HCID 90111508, compound → HCID 90110526, compound

Participants

Reaction Steps

5-Allyl-6a-(3-pyridyl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole (2.14 g, 7.40 mmol) and N,N-dimethylbarbituric acid (6.93 g, 44.41 mmol) are dissolved in chloroform (80 mL) and the resulting solution is degassed twice using liquid nitrogen. Tetrakis(triphenylphosphine)palladium (1.28 g, 1.11 mmol) is added and the mixture is stirred at room temperature for 2 hours. The reaction is concentrated under reduced pressure. The resulting residue is dissolved in a 1:1 mixture of dimethylsulfoxide/methanol (40 ml) and the solution is loaded on an ion exchange column. The material is eluted with methanol (70 mL) then with 7 M ammonia/methanol solution (70 mL). The basic fraction is collected and concentrated under reduced pressure. The product is further purified by silica gel column chromatography using a 0-15% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (1.28 g, 86%). ES/MS (m/e): 192 (M+1).

Provenance & Evidence