反应详情

To a solution of {3-hydroxy-1-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}acetonitrile (9.3 g, 22 mmol, as a mixture of diastereomers from Step 6) in methylene chloride (300 mL) at 0° C. was added Dess-Martin periodinane (10.0 g, 24 mmol). After a reaction time of 2 hours, the mixture was poured into 1N NaOH and extracted with three portions of DCM. The combined extracts were washed with further 1N NaOH, dried over sodium sulfate, decanted and the solvent removed in vacuo. Flash chromatography, eluting with a gradient from 0-10% MeOH in DCM afforded product as a yellow foam. Theoretical yield assumed for use in Step 8. 1H NMR (300 MHz, CDCl3): δ 8.85 (s, 1H), 8.50 (s, 1H), 8.35 (s, 1H), 7.42 (d, 1H), 6.80 (d, 1H), 5.68 (s, 2H), 4.11-4.00 (m, 2H), 3.74-3.61 (m, 2H), 3.59-3.50 (m, 2H), 3.31 (s, 2H), 0.96-0.88 (m, 2H), −0.06 (s, 9H); LCMS (M+H)+: 423.0.

1. extractionextracted with three portions of DCM
2. washThe combined extracts were washed with further 1N NaOH
3. dry with materialdried over sodium sulfate
4. customdecanted
5. customthe solvent removed in vacuo
6. washFlash chromatography, eluting with a gradient from 0-10% MeOH in DCM afforded product as a yellow foam