Triacetoxyperiodinane → HCID 86732041, compound

To a stirred solution of trans-(2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)cyclopropyl)methanol (16-5, 409 mg, 1.30 mmol, 1.0 eq.) in anhydrous DCM (10.0 mL) at 0° C. was added Dess-Martin periodinane (610 mg, 1.44 mmol, 1.1 eq.). The resulting mixture was stirred for 2 hours at room temperature under an atmosphere of nitrogen gas. The mixture was then quenched with saturated aqueous NaHCO3 solution (10 mL) and 10% aqueous Na2S2O3 solution (10 mL) and vigorously stirred at room temperature for 1 hour until it formed a clear two phase solution. The separated aqueous layer was extracted with DCM (2×50 mL). The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The resulting residue was purified by silica gel column chromatography (0-50% ethyl acetate in hexanes) to give trans-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)cyclopropanecarbaldehyde (16-6) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 9.55 (d, 1H, J=3.6 Hz), 7.99 (s, 1H), 2.92 (s, 3H), 2.86-2.73 (m, 2H), 2.43 (s, 3H), 1.97 (ddd, 1H, J=9.9, 5.7, 4.2 Hz), 1.85 (ddd, 1H, J=9.9, 5.7, 4.2 Hz). LRMS m/z (M+H) 312 found, 312 required.

1. customThe mixture was then quenched with saturated aqueous NaHCO3 solution (10 mL) and 10% aqueous Na2S2O3 solution (10 mL)
2. stirringvigorously stirred at room temperature for 1 hour until it
3. customformed a clear two phase solution
4. extractionThe separated aqueous layer was extracted with DCM (2×50 mL)
5. washThe combined organics were washed with brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated to dryness
9. customThe resulting residue was purified by silica gel column chromatography (0-50% ethyl acetate in hexanes)

ORD record

ord-63c26ce4c37a4dac82ca6add1ab817e5

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09200001B2