反应详情

Propane-1-sulfonic acid {2,4-difluoro-3-[hydroxy-(4-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide (P-0055, 0.215 g, 0.542 mmol) was dissolved in 40 mL of tetrahydrofuran and Dess-Martin periodinane (0.253 g, 0.597 mmol) was added. The resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate and a mixture of 20 mL of saturated aqueous sodium bicarbonate and 4 mL of saturated aqueous sodium thiosulfate was added. The mixture was vigorously stirred until the organic layer turned clear. The aqueous layer was separated and extracted once with ethyl acetate. The combined organic layers were washed with water and brine, dried with magnesium sulfate, filtered and the filtrate concentrated under vacuum. The residue was suspended in tetrahydrofuran and acetonitrile and sonicated for 15 minutes. The solid material was collected with filtration to provide the desired compound as a white solid (P-0056, 67 mg). LC-MS showed one major peak with 99.7% purity and 1H-NMR(dmso-d6) was consistent with the desired compound. MS(ESI) [M+H+]+=395.0. The filtrate was recovered and purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as an off-white solid (P40056, 51 mg). LC-MS showed one major peak with 99.8% purity. 1H-NMR(dmso-d6) was consistent with the desired compound. MS(ESI) [M+H+]+=395.0.

1. additionwas added
2. stirringThe mixture was vigorously stirred until the organic layer
3. customThe aqueous layer was separated
4. extractionextracted once with ethyl acetate
5. washThe combined organic layers were washed with water and brine
6. dry with materialdried with magnesium sulfate
7. filtrationfiltered
8. concentrationthe filtrate concentrated under vacuum
9. customacetonitrile and sonicated for 15 minutes
10. filtrationThe solid material was collected with filtration